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    • 专利摘要:
    Disclosed is a novel liquid-crystalline compound whichis a naphthalene derivative useful as an electro-optical liquidcrystal display material, a liquid crystal composition containingsuch naphthalene derivatives and a liquid crystal display devicecomprising the same. The naphthalene derivative provided by thepresent invention exhibits an excellent liquid-crystallinity andmiscibility with currently widely used liquid crystalcompositions or compositions. The addition of the naphthalenederivative makes it possible to drastically lower the thresholdvoltage of the liquid crystal composition while maintaining itshigh response. The naphthalene derivative of the presentinvention is characterized by a large birefringence index.Further, most of the naphthalene derivative of the presentinvention has no strongly polar group in its molecule and thuscan also be used for active matrix driving. Moreover, as shownin the foregoing examples, the naphthalene derivative of thepresent invention can be easily produced and is colorless andchemically stable. Accordingly, the liquid crystal compositioncomprising the naphthalene derivative of the present inventionis extremely useful as a practical liquid crystal composition,particularly a liquid crystal composition which can operatewithin a wide temperature range and requires a high speed responseand a low voltage driving.
    公开号:EP1273562A1
    申请号:EP02022912
    申请日:1999-04-22
    公开日:2003-01-08
    发明作者:Sadao Takehara；Masashi Osawa；Haruyoshi Takatsu；Makoto Negishi
    申请人:Dainippon Ink and Chemicals Co Ltd；
    IPC主号:C07C-17
    专利说明:
    [0001] The present invention relates to a novel liquid-crystallinecompound which is a naphthalene derivative useful asan electro-optical liquid crystal display material, a liquidcrystal composition containing such naphthalene derivatives anda liquid crystal display device comprising the same. BACKGROUND OF THE INVENTION
    [0002] A liquid crystal display device has been used more andmore in watch and electronic calculator as well as variousmeasuring instrument, panel for automobile, word processor,electronic note, printer, computer, television, etc.Representative examples of liquid crystal display system includeTN (twisted nematic) system, STN (super-twisted nematic) system,DS (dynamic scattering) system, GH (guest-host) system, and FLC(ferroelectric liquid crystal) system, which allows high speedresponse. Referring to driving system, multiplex driving hasbeen more common than the conventional static driving. Further,simple matrix system has been recently put into practical use.Moreover, active matrix system has been put into practical use.
    [0003] As the liquid crystal materials to be incorporated inthese liquid crystal display devices there have been synthesized a very large number of kinds of liquid-crystalline compounds todate. These liquid-crystalline compounds are used depending ontheir display Systems, driving systems or purposes. However, therequirement for improvement of the properties of liquid crystaldisplay device (enhancement of display quality or increase of thesize of display) has been growing more and more. In order tosatisfy these requirements, the development of new liquid crystalcompounds are under way.
    [0004] A liquid crystal compound is composed of a centralskeleton moiety generally called core and a terminal moiety atboth ends thereof. In general, the majority of the ring structureconstituting the core moiety of a liquid crystal compound isoccupied by 1, 4-phenylene group (which may be substituted by oneor two halogen atoms, cyano groups, methyl groups, etc.) andtrans-1,4-cyclohexylene group. However, a liquid-crystallinecompound merely made of 1,4-phenylene group and trans-1,4-cyclohexylenegroup is limited in its kind or properties. As amatter of fact, these components cannot sufficiently meet theforegoing demands.
    [0005] Besides the ring structures such as 1,4-phenylene groupand trans-1,4-cyclohexylene group, heterocyclic groups such aspyridine-2,5-diyl group, pyrimidine-2,5-diyl group and 1,3-dioxane-trans-2,5-diylgroup, condensed rings such as trans-decahydronaphthalene-2,6-diylgroup, naphthalene-2,6-diyl group, tetrahydronaphthalene-2,6-diyl group,bicycle[2,2,2]octane-1,4-diyl group and spiro[3,3]heptane-2,6-diylgroup, etc have been under study. However, few of thesecompounds have been put into practical use due to problems inproduction (technique, cost, etc.) and stability.
    [0006] Though being a ring structure which has long been reported,naphthalene-2, 6-diyl group among these condensed rings is littleknown for properties other than liquid crystallinity (phasetransition temperature), particularly nematic liquidcrystallinity, (For smectic liquid crystal, it has recently beenreported that an optically active alcohol ester ofnaphthalenecarboxylic acid exhibits interesting properties as aferroelectric liquid crystal.)
    [0007] An ordinary liquid crystal compound is terminated by achain (side chain) group at one end thereof at least. A so-calledp-type liquid crystal the dielectric anisotropy of which ispositive is mostly terminated by a polar group at the other endthereof.
    [0008] In order to lower the driving voltage in TN or STN displaysystem, a so-called strong P-type compound (the dielectricanisotropy of which is positive and great) is required. For thispurpose, a compound terminated by cyano group at the molecularend thereof and having one or more fluorine atoms in the samedirection per molecule is normally used. As a naphthalene derivative there has been reported only a compound havingphenylnaphthalene skeleton (GB2271771A: Citation (a)). There isno reference to physical properties and application.
    [0009] As the foregoing P-type compound to be used in activematrix driving there is used a compound containing as a polar groupfluorine atom, fluoroalkoxyl group or fluoroalkyl group alone.As a naphthalene derivative there is described only a compoundhaving phenylnaphthalene skeleton in GB2227019B (Citation (b))and the above Citation (a). However, there is little referenceto specific physical properties. Further, there is no referenceto application to active matrix system.
    [0010] In general, a liquid-crystalline compound which is anaphthalene derivative mostly exhibits a poor miscibility withother liquid crystal compounds. It is thought effective tointroduce side substituents (preferably fluorine atom inparticular) into the naphthalene skeleton for the purpose ofimproving the miscibility of the naphthalene derivative. Thesubstitution by fluorine atom is thought effective also if an endpolar group is directly introduced into the naphthalene ring inthe application to the foregoing active matrix system. Someexamples of such a fluoronaphthalene derivative are shown in theforegoing Citation (a). However, there is little reference toproduction process, not to mention physical properties. Thus,it is by no means thought that these exemplified compounds are actually produced compounds. Further, it cannot be presumed whatproperties these compounds have. No compounds having a structurehaving a fluoroalkoxyl group or fluoroalkyl group directlyconnected to naphthalene ring as a polar group have been known.
    [0011] It has been known that a liquid crystal compound havingan alkenyl group instead of an alkyl group, which is normally usedas a side chain moiety, exhibits excellent improvements such asimproved liquid crystallinity, reduced viscosity and improvedsharpness in display. However, these alkenyl groups are mostlyintroduced directly connected to cyclohexane ring. Thus, nocompounds having alkenyl groups introduced in naphthalene ringhave been reported.
    [0012] Similarly, no naphthalene derivatives having as sidechain alkoxylalkyl group, fluoroalkyl group, fluoroalkenyl group,fluoroalkenyloxy group, etc. have been reported.
    [0013] As groups connecting the ring structures in the coremoiety of a liquid crystal compound, there have been known manydivalent organic groups besides single bond and 1,2-ethylenegroup (-CH2CH2-).
    [0014] Liquid crystal compounds having 1,4-butylene group or1,2-propylene group are known to have a low melting point and anexcellent miscibility with other liquid crystal compounds ascompared with the corresponding liquid crystal compounds havingsingle bond or ethylene group. However, no liquid-crystalline compounds having 1,4-butylene group or 1,2-propylene group havebeen known among naphthalene derivatives.
    [0015] It has been reported that a liquid crystal compound havingdifluoroxymethylene group (-CF2O-, -OCF2-) or difluoroethenylgroup (-CF=CF-) exhibits a low viscosity and thus is effectivefor the enhancement of response. However, no such naphthalenederivatives have been known. SUMMARY OF THE INVENTION
    [0016] An object of the present invention is to provide a novelliquid-crystalline compound having a naphthalene ring and apractical liquid crystal composition comprising the same.
    [0017] The present invention has the following constitutions toaccomplish the foregoing object: 1. A naphthalene derivative represented by thefollowing general formula (I):
    [0018] In more detail, the present invention provides a novelliquid-crystalline compound which is a naphthalene derivativerepresented by the following general formula (I):
    [0019] In the foregoing general formula (I), Ra represents a C1-20alkyl, alkoxy, alkoxyalkyl, alkenyl or alkenyloxy group which maybe substituted by a C1-7 alkoxyl group or from 1 to 7 fluorine atoms.Ra preferably is a C1-7 straight-chain alkyl or alkenyl group. Thealkyl group is preferably an unsubstituted alkyl group or an alkyl group terminated by a plurality of fluorine atoms, particularlyan unsubstituted alkyl group. The alkenyl group, if the ringstructure to which it is directly connected is a saturated ring,is preferably a 1-alkenyl group or 3-alkenyl group. In this case,the double bond is preferably at the end of side chain.Alternatively, the configuration of the double bond is preferablyin trans-position. A particularly preferred example of thealkenyl group is a vinyl group or 3-butenyl group. Further, thehydrogen atom which is directly connected to the double bond ispreferably substituted by a fluorine atom. Preferred examplesof such a substituted alkenyl group include (E)-2-fluorovinylgroup, 2,3-difluorovinyl group, 3-fluoro-2-propenyl group,3,3-difluoro-2-propenyl group, 4-fluoro-3-butenyl group, and4,4-difluoro-3-butenyl group. The alkenyl group, if the ringstructure to which it is directly connected is an aromatic ring,is preferably a 3-alkenyl group. In this case, the double bondis preferably at the end of side chain. Alternatively, theconfiguration of the double bond is preferably in trans-position.A particularly preferred example of the alkenyl group is a 3-butenylgroup or trans-3-pentenyl group.
    [0020] a and b each represent 0 or 1 and satisfy the relationshipa ≥ b.
    [0021] Rings A and B each independently represent a trans-1,4-cyclohexylenegroup, 1,4-phenylene group which may be substituted by one or more fluorine atoms, pyridine-2,5-diylgroup, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group,pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group. Preferred among thesegroups are trans-1,4-cyclohexylene group, 1,4-phenylene, 2-fluoro-1,4-phenylenegroup, 3-fluoro-1,4-phenylene group,2,3-difluoro-1,4-phenylene group, 2,6-difluoro-1,4-phenylenegroup, and trans-decahydro naphthalene-2,6-diyl group. Inparticular, ring B is preferably a cyclohexane ring. Ring A, ifa strong p-type liquid crystal composition is particularlyrequired, is preferably a 2-fluoro-1,4-phenylene group or2,6-difluoro-1,4-phenylene group. If a strong n-type (negativedielectric anisotropy) is particularly required, ring A ispreferably a 3-fluoro-1,4-phenylene group or 2,3-difluoro-1,4-phenylenegroup.
    [0022] La and Lb each independently represent -CH2CH2-,-CH2CH2CH2CH2-, -CH=CH-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH(CH3)CH2-,-CH2CH(CH3)-, -CF=CF-, -CF2O-, -OCF2-, -COO-, -OCO-, -C≡C- orsingle bond. Preferred among these groups are -CH2CH2-, -CF=CF-,-CF2O-, -OCF2- and single bond, and -CH2CH2- and single bond areparticularly preferred. If La and Lb are present at the same time,at least one of them is more preferably a single bond.
    [0023] X1 to X6 each independently represent a hydrogen atom or fluorine atom. In particular, X1 preferably represents afluorine atom. If the liquid-crystalline compound is a p-typecompound, one or more of X1 to X3 each are preferably a fluorineatom while X4 to X6 each are preferably a hydrogen atom. Further,if Za is a polar group such as fluorine atom, X1 and X2 or X1 toX3 each preferably represent a fluorine atom at the same time.If the liquid-crystalline compound is a n-type compound, at leastone of X4 to X6 is preferably a fluorine atom. Alternatively, allX1 to X6 each represent a hydrogen atom. Alternatively, X1 ispreferably a fluorine atom while the others are each preferablya hydrogen atom.
    [0024] Za represents a fluorine atom, chlorine atom,trifluoromethoxy group, C1-7 alkoxyl group, C1-20 alkyl, alkoxyl,alkenyl or alkenyloxy group which may be substituted by from 1to 7 fluorine atoms or group represented by the following generalformula (IIa) or (IIb) :
    [0025] In the general formula (IIa) or (IIb), Lc and Ld eachindependently represent -CH2CH2-, -CH2CH2CH2CH2-, -CH=CH-,-CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH (CH3) CH2-, -CH2CH(CH3)-, -CF=CF-,-CF2O-, -OCF2-, -COO-, -OCO-, -C≡C- or single bond. Preferredamong these groups are -CH2CH2-, -CF=CF-, -CF2O-, -OCF2- or singlebond. Particularly preferred among these groups are -CH2CH2- orsingle bond. Further, if Lc and Ld are present at the same time,or if Lc and the foregoing La are present at the same time, atleast one of them is preferably a single bond.
    [0026] Rings C and D each independently represent a trans-1,4-cyclohexylenegroup, 1,4-phenylene group which may besubstituted by one or more fluorine atoms, pyridine-2,5-diylgroup, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group,pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group. Preferred among these groups are trans-1,4-cyclohexylene group and 1,4-phenylene groupwhich may be substituted by one or more fluorine atoms.Particularly preferred among these groups are 1, 4-phenylene group,2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group,2,3-difluoro-1,4-phenylene group, and 3,5-difluoro-1,4-phenylenegroup. In particular, if the liquid-crystallinecompound is a p-type compound, rings C and D each are preferablya 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylenegroup.
    [0027] Zb and Zc each independently represent a fluorine atom,chlorine atom, bromine atom, iodine atom, hydrogen atom; cyanogroup, -SCN, -OCN, -R', -OR', -OCOR' or -COOR', wherein R'represents a C1-20 alkyl or alkoxy group or C2-20 alkenyl oralkenyloxy group, and these groups may be susbstituted by a C1-10alkoxyl, acyl, acyloxy or alkoxycarbonyl group and one or morehydrogen atoms contained in these groups may be substituted byone or more fluorine atoms, and in the case of forming an asymmetriccarbon by the substitution or branching, it may form an opticallyactive form or racemic form.
    [0028] Preferably, Zb and Zc each represent a fluorine atom,chlorine atom, hydrogen atom, trifluoromethoxy group, C1-7 alkoxylgroup or C1-20 alkyl, alkoxyl, alkenyl or alkenyloxy group whichmay be substituted by from 1 to 20 fluorine atoms, cyanato groupor cyano group. Preferred among these groups are fluorine atom, trifluoromethoxy group, difluoromethoxy group, C1-7 straight-chainalkyl group, C1-3 straight-chain alkoxyl group, C4-7straight-chain 3-alkenyl group, C3-7 straight-chain alkenyloxygroup or cyano group. Particularly preferred among these groupsare fluorine atom, trifluoromethoxy group, methyl group, ethylgroup, propyl group, butyl group, pentyl group, methoxy group,ethoxy group, 3-butenyl group, trans-3-pentenyl group, allyloxygroup, crotyloxy group, and cyano group.
    [0029] There are the following provisions: (1) If Za represents the group represented by the generalformula (IIa), b is 0, if Za represents the group represented bythe general formula (IIb), a is 0, and if Za represents a fluorineatom, chlorine atom, trifluoromethoxy group, C1-7 alkoxyl groupor C1-20 alkyl, alkoxyl, alkenyl or alkenyloxy group which may besubstituted by from 1 to 7 fluorine atoms, a is 1; (2) If Za represents the group represented by the generalformula (IIa), ring C represents a 1, 4-phenylene group which maybe substituted by fluorine atom and Zb represents a fluorine atom,chlorine atom, trifluoromethoxy group or an alkyl or alkoxyl groupwhich may be substituted by fluorine atom, Lc represents-CH2CH2CH2CH2-, -CH=CH-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH(CH3)CH2-,-CH2CH(CH3)-, -CF=CF-, -CF2O- or -OCF2- and/or at least one of X1to X6 represents a fluorine atom; (3) If Za represents an alkyl or alkoxyl group, at least one of X1 to X6 represents a fluorine atom and/or L° represents-CH2CH2CH2CH2-, -CF=CF-, -CF2O- or -OCF2-; (4) if Za represents a fluorine or chlorine atom, Larepresents a single bond; and if ring A represents a 1,4-phenylenegroup which may be substituted by fluorine atom, b represents 0,or b represants 1 and Lb represents a single bond; and (5) If a and b each represent 0, X1 represents a fluorineatom and X2 to X6 each represent a hydrogen atom; and if Lcrepresents a single bond, Zb represents fluorine atom, chlorineatom, hydrogen atom, trifluoromethoxy group, alkenyl group,alkenyloxy group, cyanato group or cyano group.
    [0030] As mentioned, there are a variety of compoundsrepresented by the general formula (I). Preferred are thoserepresented by the following general formulae (Ia) to (Ie) asclassified by the structure of core moiety:
    [0031] Particularly preferred among the compounds representedby the general formula (Ia) are those shown below.
    [0032] Particularly preferred among the compounds representedby the general formula (Ib) are those shown below.
    [0033] Particularly preferred among the compounds representedby the general formula (Ic) are those shown below.
    [0034] Particularly preferred among the compounds representedby the general formula (Id) are those shown below.
    [0035] Particularly preferred among the compounds representedby the general formula (Ie) are those shown below.
    [0036] In the foregoing general formulae, R is as defined above,and R' represents a C1-7 straight-chain alkyl group or C2-7straight-chain alkenyl group, particularly vinyl group or 3-butenylgroup.
    [0037] Particularly preferred among the foregoing compounds arethose represented by the general formulae (Iaaa), (Iaad), (Iaae),(Iacb), (Iagb), (Iaib), (Iana), (Ianb), (Iand) , (Iapa), (Iapb),(Iata), (Iatb), (Iatd), (Iava), (Iavb), (Iawa), (Iawb), (Iawd),(IaAa), (IaAb), (IaAd), (IaCa), (IaCb), (IaGa), (IaGb), (IaGd),(IaJa), (IaJb), (IaJd), (IaNa), (IaNb), (IaNd), (IaPa) , (IaPb),(IaPd), (IaTa), (IaTb), (IaTd), (IaVa), (IaVb), (IaVd), (IaZa),(ZaZb), (IaZd), (Ibaa), (Ibab), (Ibad), (Ibca), (Ibcb), (Ibcd),(Ibea), (Ibeb), (Ibed), (Ibga), (Ibgb), (Ibgd), (Ibia), (Ibib),(Ibid), (Ibka), (Ibkb), (Ibkd), (Ibpa), (Zbpb), (Ibpd), (Ibsa),(Ibsb), (Ibsd), (Ibta), (Ibtb), (Ibtd), (Ibva), (Ibvb), (Ibvd),(Ibxa), (Ibxb), (Ibxd), (Icaa) to (Icim), and (Idaa) to (Idem).
    [0038] The compound represented by the general formula (I) ofthe present invention can be prepared by the following synthesisprocesses in combination depending on R, rings A and B, La andLb. [I] Process for the synthesis of compounds represented by thegeneral formulae (Iaaa) to (Iafe) (1) Compound prepared from a group represented by the following general formula (IIIa):
    [0039] Specific representative examples of the compound (I) ofthe present invention thus produced will be set forth in Tables1 to 3 below together with their phase transition temperature.
    [0040] The effects exerted by the incorporation of the compound(I) in the liquid crystal composition will be describedhereinafter.
    [0041] The compound represented by the general formula (Ib-1)set forth in Table 1:
    [0042] Subsequently, the nematic liquid crystal composition(M-1) was filled in a TN cell having a thickness of 4.5 µm to preparea liquid crystal device. The liquid crystal device was thenmeasured for electro-optical properties. The results are asfollows: Upper nematic phase Temperature limit (TN-1) 98.6°C Dielectric anisotropy (Δε) 4.60 Threshold voltage (Vth) 1.76 V Response (τ) 21.5 m sec.
    [0043] On the other hand, the physical properties andelectro-optical properties of the host liquid crystal (H) aloneare as follows: Upper nematic phase temperature limit (TN-1) 116.7°C Dielectric anisotropy (Δε) 4.80Threshold voltage (Vth) 1.88 V Response (τ) 21.5 m sec.
    [0044] The term "response" as used herein is meant to indicatethe response time shown during the application of voltage at whichthe rise time (τr) and the drop time (τd) are equal to each other.The results show that the compound (Ib-1) exhibits a smallerdielectric anisotropy than the host liquid crystal (H) and athreshold voltage drop of about 10% from the host liquid crystal(H) .
    [0045] The compound represented by the general formula (Ib-2)set forth in Table 1:
    [0046] TN-1 of the nematic liquid crystal composition (M-2) andthe electro-optical properties of the liquid crystal deviceprepared in the same manner as above from the composition (M-2)are as follows: Upper nematic phasetemperature limit (TN-1) 92.7°C Dielectric anisotropy (Δε) 5.7 Threshold voltage (Vth) 1.53 V Response (τ) 28.0 m sec.
    [0047] It can thus be seen that the compound (Ib-2) exhibits asmaller dielectric anisotropy than the host liquid crystal (H)and a threshold voltage drop of about 20% from the host liquidcrystal (H).
    [0048] The nematic liquid crystal composition (M-2) was thensubjected to thermal stability test and ultraviolet rayirradiation test in the same manner as the composition (M-1). Asa result, the composition (M-2) showed no change of TN-1 after thesetests. The nematic liquid crystal composition (M-2) was thenmeasured for voltage holding ratio. As a result, the composition(M-2) exhibited a sufficiently high voltage holding ratio duringpreparation, after heating and after irradiation with ultravioletrays.
    [0049] As mentioned above, the compound represented by thegeneral formula (I) is very useful in the preparation of a liquidcrystal composition having (a) a wide nematic phase operatingtemperature range, (b) a threshold voltage low enough to driveat a low voltage, (c) a quick response and (d) a voltage holdingratio high enough for active matrix driving.
    [0050] The compound represented by the general formula (Ic-7) set forth in Table 2:
    [0051] For the measurement of threshold voltage (Vth), thenematic liquid crystal composition is packed into a TN cell havinga thickness of 6 µm. The measurement is effected at a temperatureof 20°C.
    [0052] The physical properties of the nematic liquid crystalcomposition (M-3) and the electro-optical properties of the liquid crystal device prepared therefrom are as follows: TN-1 120.0°C TC-N -2°C Threshold voltage 2.06 V Dielectric anisotropy (Δε) 5.5 Birefringence index (Δn) 0.110
    [0053] It can thus be seen that the addition of the compound(Ic-7) makes it possible to raise the upper nematic phasetemperature limit (TN-1) by not lower than 3°. The nematic liquidcrystal composition (M-3) was cooled to a temperature of -60°Cto undergo crystallization. The nematic liquid crystalcomposition (M-3) thus crystallized was then measured for meltingpoint (TC-N). The results were -2°C, demonstrating that thecomposition (M-3) exhibits a melting point drop of as much as 13°from the host liquid crystal composition (H) Accordingly, thestable temperature range of nematic phase can be expanded by asmuch as about 16°. It can also be seen that the incorporationof the compound (Ic-7) makes it possible to increase thedielectric anisotropy of liquid crystal composition and lower thethreshold voltage of liquid crystal composition. The increasein the birefringence index could be suppressed to 0.02 from thatof the host liquid crystal (H).
    [0054] The liquid crystal device was then measured for voltageholding ratio at room temperature and 80°C. The results were extremely good at any of the two temperature ranges, demonstratingthat it can be sufficiently used in active matrix driving.
    [0055] A compound represented by the following general formula(R-1) having a structure similar to the compound (Ic-7) but having1,4-phenylene group instead of 2,6-naphthylene group:
    [0056] It can thus be seen that the composition (M-3) exerts abetter effect than the conventional compounds to obtain a liquidcrystal composition having a wide operating temperature range,a low threshold voltage and a proper birefringence index.
    [0057] The compound represented by the general formula (Id-1)set forth in Table 3:
    [0058] The physical properties of the compound (Id-1) and theelectro-optical properties of the liquid crystal device preparedtherefrom are as follows: TN-1 91.0°C Threshold voltage (Vth) 1.94 V Dielectric anisotropy (Δε) 4.85 Response (τr=τd) 28.4 m sec. Birefringence index (Δn) 0.112
    [0059] It can thus be seen that the incorporation of the compound(Id-1) in an amount of 20% causes a slight drop of the upper nematicphase temperature limit (TN-1) but makes it possible to lower thethreshold voltage of the liquid crystal composition anddrastically raise the birefringence index of the liquid crystalcomposition (by about 0.02 from that of the host liquid crystalcomposition (H)) without drastically deteriorating the response.Subsequently, the liquid crystal composition was allowed to standat room temperature for 1 month. However, no crystallization or phase separation were observed. It can thus be seen that thecompound (Id-1) has an excellent miscibility with theconventional liquid crystals. The liquid crystal composition(M-4) was cooled to a temperature of -15°C to undergocrystallization, and then measured for melting point (TC-N). Theresults were 14°C.
    [0060] On the other hand, a compound represented by the generalformula (R-2) having a structure similar to that of the compound(Id-1) but having a biphenyl skeleton:
    [0061] The comparison of the liquid crystal composition (HR-2) with the liquid crystal composition (H-1) shows that the liquidcrystal composition (HR-2) exhibits a slightly higher responseand a slightly lower threshold voltage (Vth). However, the uppernematic phase temperature limit (TN-1) of the liquid crystalcomposition (HR-2) showed a further drop. The liquid crystalcomposition (HR-2) also showed only a slight increase inbirefringence index.
    [0062] Subsequently, the compound represented by the generalformula (Id-2) set forth in Table 1:
    [0063] The comparison of the liquid crystal composition (M-5)with the liquid crystal composition (M-4) shows that the liquid crystal composition (M-5) exhibits a slightly lower TN-1 and aslightly reduced birefringence index but has a quick responsesimilarly to the liquid crystal composition (M-4) and a furtherdrop of threshold voltage.
    [0064] The compound represented by the general formula (Id-7)set forth in Table 3:
    [0065] It can thus be seen that the compound represented by thegeneral formula (Id-7) causes no deterioration of liquid-crystallinitydespite of the drop of melting point due to theincorporation of fluorine in naphthalene ring.
    [0066] The foregoing compound (Id-7) was added to the host liquidcrystal composition (H) in an amount of 20% by weight to prepare a liquid crystal composition (M-6). TN-1 86.0°C TC-N 12°C Threshold voltage (Vth) 1.65 V Dielectric anisotropy (Δε) 6.5 Birefringence index (Δn) 0.107 Response (τr=τd) 28.8 m sec.
    [0067] The incorporation of the compound (Id-7) in an amount of20% causes a slight drop of the upper nematic phase temperaturelimit (TN-1) but can provide a high speed response similarly tothe host liquid crystal composition (H) and makes it possible todrastically lower the threshold voltage of the liquid crystalcomposition (by 0.3 V). Further, the birefringence of the liquidcrystal composition can be drastically increased from the hostliquid crystal composition (H).
    [0068] The liquid crystal device was then measured for voltageholding ratio at room temperature and 80°C. The results were goodat any of the two temperature ranges, demonstrating that theliquid crystal device can be sufficiently used in active matrixdriving.
    [0069] It can thus be seen that the compound represented by thegeneral formula (Id) of the present invention exerts a bettereffect than the conventional compounds to obtain a low viscosity,an excellent response, a large birefringence index, a wide nematic phase operating temperature range, and a low threshold voltage.
    [0070] Accordingly, the compound (I), when used in admixturewith other nematic liquid crystal compounds, can be preferablyused as a liquid crystal material for field effect type displaycell such as TN type and STN type display cells, particularlyliquid crystal material which can operate at a wide temperaturerange and can be driven at a low voltage. Further, the compoundrepresented by the general formula (I) has no strongly polar groupin its molecule and thus can easily provide a large specificresistivity and a high voltage holding ratio. Thus, the compoundrepresented by the general formula (I) can also be used as aconstituent of liquid crystal material for active matrix driving.The present invention provides a liquid crystal compositioncomprising as a constituent at least one of the compoundsrepresented by the general formula (I) and a liquid crystal devicecomprising the liquid crystal composition.
    [0071] Specific representative examples of the nematic liquidcrystal compound which can be used in admixture with the compoundrepresented by the general formula (I) include phenyl benzoatederivative, phenyl cyclohexanecarboxylate derivative,biphenyl-4-yl cyclohexanecarboxylate derivative, phenylcyclohexanecarbonyloxybenzoate derivative, phenylcyclohexanecarboxylate derivative, phenyl cyclohexylbenzoatederivative, cyclohexyl cyclohexylbenzoate derivative, biphenyl derivative, cyclohexylbenzene derivative,terphenyl derivative, bicyclohexane derivative, 4-cyclohexylbiphenylderivative, 4-phenylbicyclohexanederivative, tercyclohexane derivative, 1,2-dicyclohexylethanederivative, 1,2-diphenylethane derivative, 1,2-diphenylethinederivative, (2-cyclohexylethyl)benzene derivative, 4-phenethylbicyclohexanederivative, 4-(2-cyclohexylethyl)biphenylderivative, 1-(4-phenyl) cyclohexyl-2-cyclohexylethanederivative, 1-(4-cyclohexylphenyl)-2-phenylethinederivative, phenylpyrimidine derivative, (4-biphenyl-4-yl)pyrimidinederivative, phenylpyridine derivative,and (4-biphenyl-4-yl)pyridine derivative. Particularlypreferred for active matrix drive among these derivatives arebiphenyl derivative, cyclohexylbenzene derivative, terphenylderivative, bicyclohexane derivative, 4-cyclohexylbiphenylderivative, 4-phenylbicyclohexane derivative, tercyclohexanederivative, 1,2-dicyclohexylethane derivative, 1,2-diphenylethanederivative, 1,2-diphenylethine derivative, (2-cyclohexylethyl)benzenederivative, 4-phenethylbicyclohexanederivative, 4-(2-cyclohexylethyl)biphenyl derivative, 1-(4-phenyl)cyclohexyl-2-cyclohexylethane derivative, and 1-(4-cyclohexylphenyl)-2-phenylethinederivative. EXAMPLES
    [0072] The present invention will be further described in thefollowing examples, but the present invention should not beconstrued as being limited thereto.
    [0073] The structure of compounds were identified by nuclearmagnetic resonance spectrum (NMR), mass spectrum (MS) andinfrared absorption spectrum (IR). The term "%" as usedhereinafter is meant to indicate % by weight. (EXAMPLE 1) Synthesis of 2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene(1-a) Synthesis of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene
    [0074] 5.7 g of magnesium was suspended in 12 ml oftetrahydrofuran. To the suspension was then added dropwise asolution of 50 g of 6-bromo-2-methoxynaphthalene in 200 ml oftetrahydrofuran at a rate such that tetrahydrofuran was gentlyrefluxed. The reaction mixture was then further stirred for 1hour. To the reaction solution was then added dropvise a solutionof 30 g of 4-propylcyclohexanone in 120 ml of tetrahydrofuran atroom temperature. The reaction mixture was then further stirredfor 1 hour. To the reaction solution was then added 200 ml ofa 10% hydrochloric acid. The reaction mixture was extracted with 300 ml of toluene, washed with water, saturated aqueous solutionof sodium bicarbonate and saturated brine, and then dried overanhydrous sodium sulfate. The solvent was then distilled off.To the residue were then added 280 ml of toluene and 4.0 g ofp-toluenesulfonic acid monohydrate. The reaction mixture wasthen heated under reflux for 3 hours. The reaction solution wasallowed to cool to room temperature, washed with water, saturatedaqueous solution of sodium bicarbonate and saturated brine, andthen dried over anhydrous sodium sulfate. The solvent was thendistilled off. The residue was then recrystallized from ethanolto obtain 44.8 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene. (1-b) Synthesis of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene
    [0075] 44.8 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalenewas dissolved in 800 ml of ethyl acetate. To thesolution was than added 10 g of 5% palladium carbon. The reactionmixture was then stirred at a hydrogen pressure of 4 kg/cm2 for6 hours. The catalyst was then removed by filtration. Thesolvent was then distilled off. The residue was then dissolvedin 180 ml of N,N-dimethylformamide. To the solution was thenadded 18 g of potassium t-butoxide. The reaction mixture was thenheated to a temperature of 120 °C with stirring for 1 hour. Thereaction solution was then allowed to cool to room temperature. To the reaction solution was then added 70 ml of a 10% hydrochloricacid to cause crystallization. The crystal thus precipitated wasfiltered off, washed with water, and then dried under reducedpressure. The crystal was then recryatallized from ethanol toobtain 28.0 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene. (1-c) Synthesis of 6-(trans-4-propylcyclohexyl)-2-naphthol
    [0076] To 28.0 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene were added 280 ml of acetic acid and280 ml of 48% hydrobromic acid. The reaction mixture was thenheated under reflux for 12 hours. The reaction solution was thenallowed to cool to room temperature. To the reaction solutionwas then added 500 ml of water to cause crystallization. Thecrystal thus precipitated was then filtered off. The crystal waswashed with water, and then dried under reduced pressure to obtain26.8 g of 6- (trans-4-propylcyclohexyl)-2-naphthol. (1-d) Synthesis of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate
    [0077] To 25.0 g of 6-(trans-4-propylcyclohexyl)-2-naphtholwere added 100 ml of dichloromethane and 30 g oftrifluoromethanesulfonic anhydride. The reaction mixture wasthen cooled to a temperature of 5°C. To the reaction mixture wasthen added a solution of 11.0 g of pyridine in 40 ml ofdichloromethane at a rate such that the resulting temperature didn't exceed 20°C. After the termination of dropwise addition,the reaction mixture was returned to room temperature withstirring. To the reaction mixture was then added 150 ml of water.The resulting organic phase was washed with water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solventwas then distilled off. The residue was then purified throughsilica gel column chromatography (solvent: dichloromethane) toobtain 36.7 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethane sulfonate. (1-e) Synthesis of 2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene
    [0078] 1.0 g of magnesium was suspended in 2 ml oftetrahydrofuran. To the suspension was then added dropwise asolution of 7.0 g of 3,4-difluoro-1-bromobenzene in 35 ml oftetrahydrofuran at a rate such that tetrahydrofuran was gentlyrefluxed. The reaction mixture was then further stirred at roomtemperature for 1 hour. Excessive magnesium was removed byfiltration. The reaction solution was then added dropwise to asolution of 10.0 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethane sulfonateand 0.3 g of tetrakis(triphenylphosphine)palladium in 50 ml oftetrahydrofuran at room temperature. The reaction mixture wasthen stirred at room temperature for 1 hour. To the reactionmixture was then added 100 ml of water. The reaction mixture was extracted with 200 ml of toluene, washed with water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solventwas then distilled off. The residue was purified through silicagel column chromatography (hexane), and then recrystallized fromethanol to obtain 7.1 g of a purified material. (Cr 90 N 200.5I)
    [0079] The following compounds were similarly obtained. 2-(3,4-Difluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 2-(3,4-Difluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 2-(3,4-Difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 2- (3,4,5-Trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 2-(3,4,5-Trifluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 2-(3,4,5-trifluorophenyl) -6-(trans-4-butylcyclohexyl)naphthalene 2-(3,4,5-Trifluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene
    [0080] To 25.0 g of 6-(3,4,5-trifluorophenyl)-2-hydroxynaphthalenewere added 200 ml of dichloromethane and 34.0g of trifluoromethanesulfonic anhydride. The reaction mixturewas then cooled to a temperature of 5°C. To the reaction mixturewas then added a solution of 12.0 g of pyridine in 48 ml ofdichloromethane at a rate such that the resulting temperaturedidn't exceed 20°C. After the termination of dropwise addition,the reaction mixture was returned to room temperature withstirring. To the reaction mixture was then added 200 ml of water.The resulting organic phase was washed with water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solventwas then distilled off. The residue was then purified throughsilica gel column chromatography (dichloromethane) to obtain 37.3g of 6-(3,4,5-trifluorophenyl)naphthalene-2-yltrifluoromethanesulfonate. (2-b) Synthesis of 2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalene
    [0081] 25.0 g of 6-(3,4,5-trifluorophenyl)naphthalene-2-yltrifluoromethanesulfonate and 1-ethynyl-4-propylcyclohexanewere dissolved in a mixture of 125 ml of N,N-dimethylformamideand 25 ml of triethylamine. To the solution were then added 0.7g of tetrakis(triphenylphosphine)palladium and 0.2 g of copper iodide (I). The reaction mixture was then stirred at atemperature of 50°C for 3 hours. The reaction solution was thenallowed to cool to room temperature. To the reaction solutionwas then added 150 ml of water. The reaction solution wasextracted with 200 ml of toluene, washed with water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solventwas then distilled off. The residue was then recrystallized fromethanol to obtain 17.6 g of 2-(trans-4-propylcyclohexyl)ethynyl-6- (3,4-, 5-trifluorophenyl)naphthalene. (2-c) Synthesis of 2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl] naphthalene
    [0082] 17.6 g of 2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalenewas dissolved in 400 ml oftetrahydrofuran. To the solution was then added 5 g of 5%palladium carbon. The reaction mixture was then stirred at ahydrogen pressure of 5 kg/cm2 for 6 hours. The catalyst was thenremoved by filtration. The solvent was then distilled off. Theresidue was purified through silica gel column chromatography(hexane) , and then recrystallized from ethanol to obtain 11.5 gof a purified product. (Cr 62 N 134 I)
    [0083] The following compounds were prepared in the same manneras mentioned above. 2- (3,4,5-Trifluorophenyl)-6- [2-(trans-4-ethylcyclohexyl) ethyl] naphthalene 2-(3,4,5-Trifluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 2- (3,4,5-Trifluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 2-(3,4-Difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl] naphthalene 2-(3,4-Difluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthaleneCr 110 N 166 I 2- (3,4-Difluorophenyl)-6-[2- (trans-4-butylcyclohexyl)ethyl]naphthalene 2-(3,4-Difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene
    [0084] The Grignard reaction of Example (1-a) was followedexcept that 1,4-cyclohexadione monoethylene acetal was usedinstead of 4-propylcyclohexanone. The reaction product was thendehydrated with potassium hydrogensulfate. To the toluenesolution was then added ethylene glycol. The reaction mixturewas then heated under reflux while the azeotropically distilledwater was being driven out of the system. The reaction solutionwas allowed to cool to room temperature, washed sequentially with water, saturated aqueous solution of sodium bicarbonate andsaturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was then distilled off to obtain4- (6-methoxynaphthalene-2-yl) -3-cyclohexenone ethylene acetal.The product was dissolved in toluene, and then subjected tocatalytic reduction in the same manner as (1-b). To the reactionsolution was then added formic acid. The reaction mixture washeated with stirring, and then cooled. To the reaction solutionwas then added water. The resulting toluene phase was then washed.The solvent was then distilled off. The resulting crude crystalwas then recrystallized from ethanol to obtain 4-(6-methoxynaphthalene-2-yl)cyclohexanone in crystal form. The crystalthus obtained was dissolved in a mixture of toluene and THF, andthen cooled. To the reaction solution was then added a Wittigreagent prepared from methoxymethyltriphenylphosphonium bromideand potassium t-butoxide. The reaction mixture was then returnedto room temperature. To the reaction mixture were then addedwater and hexane. Insoluble matters were then removed from theresulting hexane phase by filtration. The residue was then washedwith a mixture of water and methanol. The solvent was thendistilled off. The residue was then dissolved in THF. To thesolution was then added diluted hydrochloric acid. The reactionsolution was heated under reflux for 1 hour, and then cooled. Tothe reaction solution was then added water. The reaction solution was then extracted with ethyl acetate. The solvent was thendistilled off. The residue was then dissolved in ethanol. Tothe solution was then added a 20% aqueous solution of sodiumhydroxide. The reaction mixture was then stirred at roomtemperature. To the reaction solution was then added water. Thereaction solution was extracted with toluene, washed, and thendried. The solvent was then distilled off to obtain trans-4-(6-methoxynaphthalene-2-yl)cyclohexanecarbaldehydein crystalform. The crystal thus obtained was dissolved in THF. To thereaction solution was then added a Wittig reagent prepared frommethyltriphenylphosphonium iodide and potassium t-butoxide.The reaction mixture was then returned to room temperature. Tothe reaction mixture were then added water and hexane. Insolublematters were then removed from the resulting hexane phase byfiltration. The residue was washed with a mixture of water andmethanol, and then dried. The solvent was then distilled off.The residue was then purified through silica gel columnchromatography (toluene) to obtain 2-(trans-4-vinylcyclohexyl)-6-nethoxynaphthalenein crystal form. Thecrystal was then processed in the same manner as (1-c), (1-d) and(1-e) to obtain the titled 2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene.
    [0085] The following compounds were prepared in the same manneras mentioned above. 2-(3,4-Difluorophenyl)-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene 2-(3,4,5-Trifluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 2-(3,4,5-Trifluorophenyl)-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene
    [0086] To a solution of 200 g of 2-bromo-6-methoxynaphthaleneand 2.5 g of dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II) in 200 ml of tetrahydrofuran (THF) was added dropwise aGrignard reagent prepared from 125 g of propyl bromide and 27 gof magnesium under nitrogen atomsphere. The reaction mixture wasfurther stirred for 1 hour, and then poured into water. To thereaction mixture was then added diluted hydrochloric acid. Theresulting organic phase was then separated. The resultingaqueous phase was extracted with toluene. The organic phase andthe material thus extracted were together washed sequentiallywith water, saturated aqueous solution of sodium bicarbonate,water and saturated brine, and then dehydrated and dried overanhydrous sodium sulfate. The solvent was then distilled off toobtain 172 g of 2-methoxy-6-propylnaphthalene. (4-b) Synthesis of 6-propyl-2-naphthol
    [0087] The total amount (172 g) of 2-methoxy-6-propylnaphthaleneobtained in the process (4-a) was added to amixture of 680 ml of acetic acid and 680 ml of a 48% hydrobromicacid. The reaction mixture was heated under reflux for 8 hours.The reaction solution was then allowed to cool to room temperature.To the reaction solution was then added 1,300 ml of water. Theresulting crystal was filtered off, and then washed with water.The resulting crystal was dissolved in 1,000 ml of ethyl acetate,and then washed sequentially with water, saturated aqueoussolution of sodium bicarbonate, water and saturated brine. Theproduct was then dehydrated and dried over anhydrous sodiumsulfate. The solvent was then distilled off to obtain 152 g of6-propyl-2-naphthol in the form of crude crystal form. (4-c) Synthesis of 1-fluoro-6-propyl-2-naphthol
    [0088] To a solution of 20 g of 6-propyl-2-naphthol and 1.8 gof sodium trifluoromethanesulfonate in 80 ml of dichloromethanewas added 23.7 g of N,N'-difluoro-2,2'-dipyridiniumbistetrafluoroborate. The reaction mixture was then stirred for8 hours. The reaction solution was then poured in water. To thereaction mixture was then added diluted hydrochloric acid. Theresulting organic phase was then separated. The resultingaqueous phase was extracted with toluene. The organic phase andthe material thus extracted were together washed sequentially with water and saturated brine, and then dehydrated and dried overanhydrous sodium sulfate. The solvent was distilled off to obtainan oily matter which was then purified through silica gel columnchromatography (hexane/ethyl acetate = 9/1) to obtain 17.1 g of1-fluoro-6-propyl-2-naphthol. (4-d) Synthesis of 1-fluoro-6-propylnaphthalene-2-yltrifluoromethanesulfonate
    [0089] The total amount (17.1 g) of 1-fluoro-6-propyl-2-naphtholobtained in the process (4-c) and 25.1 g oftrifluoromethanesulfonic anhydride were dissolved in 80 ml ofdichloromethane. To the solution was then added dropwise 15.9ml of pyridine. The reaction mixture was then further stirredfor 1 hour. To the reaction solution was then added dilutedhydrochloric acid. The resulting organic phase was separated.The resulting aqueous phase was then extracted with toluene. Theorganic phase and the material thus extracted were washedsequentially with water and saturated brine, and then dehydratedand dried over anhydrous sodium sulfate. The solvent wasdistilled off to obtain a crystal which was then purified thoughsilica gel column chromatography to obtain 24.2 g of 1-fluoro-6-propylnaphthalene-2-yltrifluoromethanesulfonate. (4-e) Synthesis of l-fluoro-2-(3,4-difluorophenyl)-6-propylnaphthalene
    [0090] 20 g of 1-fluoro-6-propylnaphthalene-2-yl trifluoromethanesulfonate obtained in the process (4-d) anddibromobis(triphenylphosphine)nickel (II) were dissolved in 80ml of THF. To the solution was added dropwise a Grignard reagentprepared from 25.8 g of 3,4-difluorobromobenzene and 3.2 g ofmagnesium under a nitrogen atomsphere. The reaction mixture wasfurther stirred for 1 hour. To the reaction solution was thenadded diluted hydrochloric acid. The resulting organic phase wasthen separated. The resulting aqueous phase was then extractedwith toluene. The organic phase-and the material thus extractedwere together washed sequentially with water, saturated aqueoussolution of sodium bicarbonate and saturated brine, and thendehydrated and dried over anhydrous sodium sulfafe. The solventwas then distilled off to obtain a crystal. The crystal thusobtained was purified through silica gel column chromatography(hexane), and then subjected to distillation to obtain 6.5 g of1-fluoro-2-(3,4-difluorophenyl)-6-propylnaphthalene. Cr - 16 N13 I
    [0091] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,4-difluorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-butylnaphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl) -6-ethylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-propylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-butylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-propylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-butylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluorophenyl)-6-propylnaphthalene 1-Fluoro-2-(3-fluorophenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluorophenyl)-6-heptylnaphthalene l-Fluoro-2-(3-fluorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-propylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-butylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl) -6-pentylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl) -6-heptylnaphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-phenyl-6-ethylnaphthalene 1-Fluoro-2-phenyl-6-propylnaphthalene 1-Fluoro-2-phenyl-6-butylnaphthalene 1-Fluoro-2-phenyl-6-pentylnaphthalene 1-Fluoro-2-phenyl-6-hexylnaphthalene 1-Fluoro-2-phenyl-6-heptylnaphthalene 1-Fluoro-2-phenyl-6-(3-butenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-chlorophenyl)-6-propylnaphthalene 1-Fluoro-2-(4-chlorophenyl)-6-butylnaphthalene l-Fluoro-2-(4-chlorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-chlorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-chlorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-propylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(3-butenyl)-naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-propylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl) -6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl) -6-pentylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl) -6-heptylnaphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl) -6-ethylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl) -6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl) -6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl) -6-(3-butenyl)naphthalene 1-Fluoro-2- (4-difluoromethoxyphenyl) -6-ethylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(3-butenyl) naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-ethylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-(3-butenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-propylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl) -6-propylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl) -6-pentylnaphthalene 1-Fluoro-2- (3-fluoro-4-trifluoromethylphenyl) -6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl) -6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenylphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2- (3,5-difluoro-4-trifluoromethylphenyl)-6-ethylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-propylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl) -6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenylphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-methoxyphenyl) -6-propylnaphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-methoxyphenyl) -6-pentylnaphthalene 1-Fluoro-2-(4-methoxyphenyl) -6-hexylnaphthalene 1-Fluoro-2-(4-methoxyphenyl) -6-heptylnaphthalene 1-Fluoro-2-(4-methoxyphenyl) -6-(3-butenyl) naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl) -6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl) -6-propylnaphthalene 1-Fluoro-2- (3-fluoro-4-methoxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-ethylnaphthalene 1-Fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6-propylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl) -6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl) -6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl) -6-(3-butenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-propylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(3-butenyl)naphthalene 1-Fluoro-2-(4-methylphenyl) -6-ethylnaphthalene 1-Fluoro-2-(4-methylphenyl)-6-propylnaphthalene 1-Fluoro-2-(4-methylphenyl)-6-butylnaphthalene 1-Fluoro-2-(4-methylphenyl) -6-pentylnaphthalene 1-Fluoro-2-(4-methylphenyl) -6-hexylnaphthalene 1-Fluoro-2-(4-methylphenyl)-6-heptylnaphthalene 1-Fluoro-2-(4-methylphenyl)-6- (3-butenyl) naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4- (3,4-difluorophenyl)phenyl] -6-ethylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-propylnaphthalene1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4- (4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2- [4- (3-fluoro-4-chlorophenyl)phenyl] -6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4- (3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4- (4-trifluoromethoxyphenyl)phenyl] -6-heptylnaphthalene 1-Fluoro-2-[4- (4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2- [4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2- [4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2- [4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2- [4- (3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]- 6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl] -6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4- (4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]- 6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-(3-butenyl) naphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2- [4- (3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4- (4-allyloxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl)-phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(4-methylphenyl) -6-(3-butenyl)naphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-[4- (3-butenyl)phenyl]phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl)-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2- [3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl) naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4- (4-trifluoromethylphenyl)phenyl] -6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl) naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2- [3-fluoro-4- (3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4- (3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6- (3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Flubro-2- [3-fluoro-4- (3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl) naphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4- (3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2- [3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl]phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6- (3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4- (3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4- (3,5-difluorophenyl)phenyl] -6- (3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4- (4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]- 6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl] -6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl] -6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2- [3,5-difluoro-4- (3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl]phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl] -6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2- [3,5-difluoro-4- (3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl) naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl] -6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2- [3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2- [3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4- (4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl) phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl)-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4- (4-allyloxyphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4- (4-methylphenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene l-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene
    [0092] 22.6 g of magnesium was suspended in 30 ml of THF. Tothe suspension was then added dropwise a solution of 20 g of2-bromo-6-methoxynaphthalene in 100 ml of THF at a rate such thatTHF was gently refluxed in about 2 hours. The reaction mixturewas then further stirred for 1 hour. To the reaction solutionwas then added dropwise a solution of 130.1 g of 4-propylcyclohexanonein 520 ml of THF in 1 hour. The reactionmixture was further stirred for 2 hours. To the reaction solutionwas then added 200 ml of a 10% hydrochloric acid. To the reactionmixture was then added 200 ml of hexane. The resulting organicphase was then separated. The resulting aqueous phase was thenextracted with 100 ml of hexane. To the material thus extractedwas then added the organic phase. The mixture was washed withwater, saturated aqueous solution of sodium bicarbonate andsaturated brine, and then dried over anhydrous sodium sulfate.The solvent was distilled off. To the residue were then added280 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate.The reaction mixture was then heated under reflux for 3 hours.The reaction solution was allowed to cool to room temperature,washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydroussodium sulfate. The solvent was then distilled off to obtain 260g of an oily cyclohexanol derivative. The total amount of thecyclohexanol derivative thus obtained was then dissolved in 800ml of toluene. To the solution was then added 16.1 g of p-toluenesulfonicmonohydrate. The reaction mixture was thenheated to a temperature of 110°C with stirring while the distilledwater was being removed away. After the termination ofdistillation of water, the reaction solution was then returnedto room temperature. To the reaction solution was then added 300ml of water. The resulting organic phase was then separated. Theorganic phase thus separated was washed with saturated aqueoussolution of sodium bicarbonate, water and saturated brine, andthen dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 246 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalenein the form of an oilycrude product. (5-b) Synthesis of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene
    [0093] The total amount of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthaleneobtained in the process (5-a) was dissolvedin 1.2 1 of ethyl acetate. To the solution was then added 47 gof 5% palladium/carbon (hydrous). The reaction mixture was thenstirred in an autoclave at a hydrogen pressure of 4 kg/cm2. The reaction mixture was then stirred at room temperature for 5 hours.The catalyst was then removed by filtration through Celite. Thesolvent was then distilled off to obtain 260 g of a trans/cismixture of 2-methoxy-6-(4-propylcyclohexyl)naphthalene. Thetotal amount of the product was then dissolved in 1.3 l ofN,N-dimethylformamide (DMF). To the solution was then added 125g of potassium t-butoxide. The reaction mixture was then heatedunder reflux for 5 hours. The reaction solution was then allowedto cool to room temperature. To the reaction solution was thenadded 200 ml of water. The reaction solution was then extractedtwice with 200 ml of toluene. The material thus extracted andthe organic phase were together washed with diluted hydrochloricacid, saturated aqueous solution of sodium bicarbonate, water andsaturated brine, and then dried over anhydrous sodium sulfate.The solvent was distilled off. The residue was purified throughsilica gel column chromatography (toluene), and thenrecrystallized twice from ethanol to obtain 115 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalenein the form ofwhite crystal. (5-c) Synthesis of 6-(trans-4-propylcyclohexyl)-2-naphthol
    [0094] To the total amount of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthaleneobtained in the process (5-b) wereadded 700 ml of acetic acid and 700 ml of a 48% hydrobromic acid.The reaction mixture was then heated under reflux for 20 hours. The reaction solution was then allowed to cool to room temperature.To the reaction solution was then added 200 ml of water. Thereaction solution was then extracted twice with 400 ml of toluene.The material thus extracted and the organic phase were togetherwashed with water and then with saturated brine, and thendehydrated and dried over anhydrous sodium sulfate. The solventwas then distilled off to obtain 109 g of 6-(trans-4-propylcyclohexyl)-2-naphtholin the form of white crystal. (5-d) Synthesis of 1-fluoro-6-(trans-4-propylcyclohexyl)-2-naphthol
    [0095] The total amount of 6-(trans-4-propylcyclohexyl)-2-naphtholobtained in the process (5-c) was dissolved in 500 mlof dichloromethane. To the solution was then added 7 g of sodiumtrifluoromethanesulfonate. The reaction mixture was thenvigorously stirred. To the reaction solution was then addedgradually 86.7 g of N,N'-difluoro-2,2'-dipyridiniumbistetrafluoroborate. The reaction mixture was then furtherstirred at room temperature for 5 hours. To the reaction solutionwere added water and then a 10% aqueous solution of sodiumhydroxide so that excess fluorinating agent was decomposed. Thereaction solution was then returned to acidity with dilutedhydrochloric acid. The resulting organic phase was thenseparated. The resulting aqueous phase was then extracted with100 ml of anhydrous sodium sulfate. The material thus extracted and the organic phase were together washed with water and thenwith saturated brine, and then dehydrated and dried over sodiumsulfate. The solvent was distilled off to obtain 131.5 g of acrude crystal which was then purified through silica gel columnchromatography (toluene) to obtain 83 g of 1-fluoro-6-(trans-4-proopylcyclohexyl)-2-naphtholin the form of white crystal.(5-e) Synthesis of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate
    [0096] The total amount of 1-fluoro-6-(trans-4-propylcyclohexyl) -2-naphthol obtained in the process (5-d) was dissolved in450 ml of dichloromethane. To the solution was added 55.3 ml oftrifluoromethanesulfonic anhydride to make a suspension which wasthen cooled to a temperature of 5°C. To the suspension was thenadded dropwise 54 ml of pyridine with vigorous stirring. Thereaction mixture was then further stirred for 1 hour. To thereaction mixture was then added 100 ml of water to terminate thereaction. The resulting organic phase was then separated. Theresulting aqueous phase was then extracted with 100 ml ofdichloromethane. The material thus extracted and the organicphase were together washed sequentially with diluted hydrochloricacid, saturated aqueous solution of sodium bicarbonate, water andsaturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was distilled off to obtain 105 gof a crude crystal which was then purified through silica gel column chromatography (hexane) to obtain 96 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate inthe form of white crystal. (5-f) Synthesis of 1-fluoro-2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene
    [0097] 1 g of magnesium was suspended in 1 ml of THF. To thesuspension was then added dropwise a solution of 7.9 g of3,4-difluoro-1-bromobenzene in 32 ml of THF at a rate such thatTHF was gently refluxed. The reaction mixture was then stirredat room temperature for 1 hour. Excess magnesium was then removedby filtration. The residue was then added dropwise to a solutionof 10 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate obtained in the process (2-e) and 0.5g of dibromobis(triphenylphosphine)nickel (II) in 40 ml of THFat a temperature of 40°C. The reaction mixture was then stirredfor 1 hour. To the reaction mixture was then added 50 ml of water.The reaction mixture was extracted with 50 ml of toluene, washedwith water and saturated brine, and then dried over anhydroussodium sulfate . The solvent was then distilled off. The residuewas purified through silica gel column chromatography (hexane),and then recrystallized from ethanol to obtain 2.6 g of purified1-fluoro-2-(3,4-difluorophenyl) -6- (trans-4-propylcyclohexyl)naphthalene.(Cr 85 N 198.5 I)
    [0098] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl) -6- (trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2- (3,5-difluorophenyl) -6- (trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2- (3,5-difluorophenyl) -6- (trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-heptylcyclohexyl) naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2- (4-difluoromethoxyphenyl) -6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-difluoromethoxyphenyl) -6- (trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-difluoromethoxyphenyl) -6- (trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2- (3,5-difluoro-4-difluoromethoxyphenyl)-6- (trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6- (trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6- (trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6- (trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-trifluoromethylphenyl) -6- (trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl) -6- (trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl) -6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6- (trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2- (4-methoxyphenyl) -6- (trans-4-pentylcyclohexyl) naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-methoxyphenyl) -6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-methoxyphenyl) -6- (trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl) -6- (trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2- (4-allyloxyphenyl) -6- (trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-propylcyclohexyl)naphthalene 1-Fluoro-2-[4- (3-butenyl)phenyl]-6- (trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2- [4-(3-butenyl)phenyl]-6- (trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-heptylcyclohexyl)naphthalene
    [0099] The procedure of Example 5 was followed except thattrans-4-propylcyclohexane ethanol was used instead of 4-propylcyclohexanoneand isomerization in the process (5-b) wasnot effected to obtain l-fluoro-2-(3,4-difluorophenyl)-6-[2-(trana-4-propylcyclohexylethyl]naphthalenein the form of whitecrystal.
    [0100] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl] naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene. 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (3,4,5-trifluorophenyl) -6- [2- (trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-5-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (3-fluoro-4-chlorophenyl) -6- [2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (3-fluoro-4-chlorophenyl) -6-[2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethoxyphenyl) -6- [2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethoxyphenyl) -6- [2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (4-difluoromethoxyphenyl) -6- [2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (3-fluoro-4-difluoromethoxyphenyl) -6- [2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6- [2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethylphenyl) -6- [2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethylphenyl) -6- [2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-[3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- (3,5-difluoro-4-trifluoromethylphenyl) -6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2- (trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-ethylcyclohexyl)ethyl] naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- [4-(3-butenyl)phenyl]-6- [2- (trans-4-butylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- [4-(3-butenyl)phenyl]-6- [2- (trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene 1-Fluoro-2- [4- (3-butenyl)phenyl]-6- [2- (trans-4-heptylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6- [2- (4-butylphenyl) ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-phenyl-6- [2- (4-hexylphenyl) ethyl]naphthalene 1-Fluoro-2-phenyl-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-hexylphenyl) ethyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl) -6- [2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethoxyphenyl) -6- [2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl) -6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2- (3-fluoro-4-trifluoromethoxyphenyl) -6-[2- (4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl) -6- [2- (4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6- [2- (4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl) -6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl) -6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2- (3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-[2- (4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl) -6-[2- (4-propylphenyl)ethyl]naphthalene 1-Fluoro-2- (4-trifluoromethylphenyl) -6- [2- (4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl) -6- [2- (4-propylphenyl)ethyl]naphthalene 1-Fluoro-2- (3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2- (3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-[3,5-difluoro-4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-pentylphenyl)ethyl] naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-(4-methylphenyl) -6- [2-(4-heptylphenyl) ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-ethylphenyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-propylphenyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-butylphenyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-pentylphenyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-hexylphenyl)ethyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-heptylphenyl)ethyl]naphthalene
    [0101] 50 g of 6-bromo-2-naphthol and 48 g of 4-propylphenylboricacid (synthesized by reacting a Grignardreagent prepared from 4-propylbromobenzene with trimethyl borate,and then subjecting the reaction product to hydrolysis withhydrochloric acid) were dissolved in a mixture of 200 ml of tolueneand 100 ml of ethanol. To the solution was then added 200 ml ofa 2 N aqueous solution of potassium carbonate. To the reactionmixture was then added 2.6 g oftetrakis (triphenylphophine)palladium (0). The reaction mixturewas then heated under reflux for 6 hours. The reaction solutionwas then allowed to cool to room temperature. The resultingorganic phase was then separated. The resulting aqueous phasewas then extracted with toluene. The material thus extracted andthe organic phase were together washed sequentially with dilutedhydrochloric acid, water and saturated brine, and then dehydratedand dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 47 g of 6-(4-propylphenyl)-2-naphthol incrystal form.
    [0102] The crystal thus obtained was then processed in the samemanner as (5-d) and (5-e) to obtain 1-fluoro-2-(3,4,5-trifluorophenyl)-6-(4-propylphenyl)naphthalenein the form of white crystal.
    [0103] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,4-difluorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,4-difluorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(4-heptylphenyl) naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-phenyl-6-(4-ethylphenyl) naphthalene 1-Fluoro-2-phenyl-6-(4-propylphenyl)naphthalene 1-Fluoro-2-phenyl-6-(4-butylphenyl)naphthalene 1-Fluoro-2-phenyl-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-phenyl-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-phenyl-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-phenyl-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl) -6- (4-heptylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2- (4-trifluoromethoxyphenyl) -6-[4- (3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2- (3-fluoro-4-trifluoromethoxyphenyl) -6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2- (3,5-difluoro-4-trifluoromethoxyphenyl) -6- (4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl) -6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-ethylphenyl) naphthalene 1-Fluoro-2- (4-difluoromethoxyphenyl)-6-(4-propylphenyl) naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6- (4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6- (4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2- (3-fluoro-4-difluoromethoxyphenyl)-6- (4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl) -6- (4-butylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenylphenyl)-6-[4- (3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenylphenyl) -6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[4-(3-butenyl)penyl]naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-pentylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(4-ethylphenyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(4-propylphenyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(4-butylphenyl)naphthalene 1-Fluoro-2-(4-methylphenyl) -6-(4-pentylphenyl) naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(4-hexylphenyl)naphthalene 1-Fluoro-2-(4-methylphenyl)-6-(4-heptylphenyl)naphthalene 1-Fluoro-2- (4-methylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6- (4-ethylphenyl) naphthalene 1-Fluoro-2- [4-(3-butenyl)phenyl]-6-(4-propylphenyl) naphthalene 1-Fluoro-2-[4-(3-butenyl) phenyl]-6- (4-butylphenyl) naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-pentylphenyl) naphthalene 1-Fluoro-2- [4- (3-butenyl)phenyl]-6- (4-hexylphenyl) naphthalene 1-Fluoro-2-[4- (3-butenyl) phenyl]-6- (4-heptylphenyl) naphthalene 1-Fluoro-2- [4-(3-butenyl)phenyl]-6-[4-(3-butenyl)phenyl]naphthalene
    [0104] The Grignard reaction of Example 5 was followed exceptthat 1,4-cyclohexadione monoethylene acetal was used instead of4-propylcyclohexanone. The reaction product was then dehydratedwith potassium hydrogensulfate instead of p-toluenesulfonic acid,To the toluene solution was then added ethylene glycol. Thereaction mixture was then heated under reflux while theazeotropically distilled water was being driven out of the system.The reaction solution was allowed to cool to room temperature,washed sequentially with water, saturated aqueous solution ofsodium bicarbonate and saturated brine, and then dehydrated anddried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 4-(6-methoxynaphthalene-2-yl)-3-cyclohexenoneethylene acetal. The product was dissolved intoluene, and then subjected to catalytic reduction in the samemanner as (2-b) . To the reaction solution was then added formicacid. The reaction mixture was heated with stirring, and thencooled. To the reaction solution was then added water. Theresulting toluene phase was then washed. The solvent was thendistilled off. The resulting crude crystal was thenrecrystallized from ethanol to obtain 4-(6-methoxynaphthalene-2-yl)cyclohexanone in crystal form. The crystalthus obtained was dissolved in a mixture of toluene and THF, and then cooled. To the reaction solution was then added a Wittigreagent prepared from methoxymethyltriphenylphosphonium bromideand potassium t-butoxide. The reaction mixture was then returnedto room temperature. To the reaction mixture were then addedwater and hexane. Insoluble matters were then removed from theresulting hexane phase by filtration. The residue was then washedwith a mixture of water and methanol. The solvent was thendistilled off. The residue was then dissolved in THF. To thesolution was then added diluted hydrochloric acid. The reactionsolution was heated under reflux for 1 hour, and then cooled. Tothe reaction solution was then added water. The reaction solutionwas then extracted with ethyl acetate. The solvent was thendistilled off. The residue was then dissolved in ethanol. Tothe solution was then added a 20% aqueous solution of sodiumhydroxide. The reaction mixture was then stirred at roomtemperature. To the reaction solution was then added water. Thereaction solution was extracted with toluene, washed, and thendried. The solvent was then distilled off to obtain trans-4-(6-methoxynaphthalene-2-yl)cyclohexanecarbaldehyde in crystalform. The crystal thus obtained was dissolved in THF. To thereaction solution was then added a Wittig reagent prepared frommethyltriphenylphosphonium iodide and potassium t-butoxide.The reaction mixture was then returned to room temperature. Tothe reaction mixture were then added water and hexane. Insoluble matters were then removed from the resulting hexane phase byfiltration. The residue was washed with a mixture of water andmethanol, and then dried. The solvent was then distilled off.The residue was then purified through silica gel columnchromatography (toluene) to obtain 2-(trans-4-vinylcyclohexyl)-6-methoxynaphthalenein crystal form. Thecrystal was then processed in the same manner as (5-c), (5-d) and(5-e) to obtain the titled 2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene.
    [0105] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-phenyl-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2- (3-fluoro-4-trifluoromethoxyphenyl) -6- (trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene. 1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl) -6- (trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-allyloxyphenyl)-6- (trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-(4-methylphenyl) -6- (trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-vinylcyclohexyl)naphthalene
    [0106] 1-Fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-(trans-4-propylcyclohexyl)naphthalene (obtainedin the same manner as (5-f) except that 2-(4-bromophenyl)-.4,4-dimethyl-1,3-oxazolidinewas used instead of 3,4-difluoro-1-bromobenzene)was dissolved in 50 ml of pyridine. Tothe solution was then added dzopwise 5.6 g of phosphorusoxychloride at a temperature of 25°C. The reaction mixture wasthen stirred at a temperature of 110°C for 5 hours. Excessphosphorus oxychloride was then distilled off under reducedpressure. To the residue was then added diluted hydrochloric acid.The resulting aqueous phase was then extracted with toluene. Thematerial thus extracted and the organic phase were together washedwith water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was then distilled off. The residuewas purified through silica gel column chromatography (hexane),and then recrystallized from ethanol to obtain 4.4 g of the titledcompound.
    [0107] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene
    [0108] 20 g of 1-fluoro-2-(3-fluoro-4-hydroxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene (obtained in the samemanner as in (5-f) except that 1-bromo-3-fluoro-4-methoxybenzenewas used instead of 3,4-difluoro-1-bromobenzene to obtain 1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6- (trans-4-propylcyclohexyl)naphthalenewhich was then demethylated withhydrobromic acid) was dissolved in 80 ml of dichloromethane. Tothe solution was then added dropwise 15.8 g oftrifluoromethanesulfonic anhydride under cooling with ice. Tothe reaction mixture was then added dropwise 10 ml of pyridinein such a manner that the temperature thereof didn't exceed 5°C.After the termination of dropwise addition, the reaction mixturewas stirred at the same temperature for 1 hour. To the reactionmixture was then added 20 ml of water to terminate the reaction.The resulting organic phase was washed twice with 20 ml of water,and then dehydrated and dried over anhydrous sodium sulfate.Subsequently, the solvent was distilled off. The residue was thenpurified through silica gel column chromatography (hexane) toobtain 24.3 g of 1-fluoro-2-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene. (10-b) Synthesis of 1-fluoro-2-(3-fluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene
    [0109] The total amount of 1-fluoro-2-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene obtained in the process (10-a) wasdissolved in 100 ml of acetonitrile. To the solution were thanadded 1.2 g of dibromobis(triphenylphosphine)nickel (II), 1 g oftriphenyl phosphine, 0.25 g of zinc powder and 6.2 g of potassiumcyanide. The reaction mixture was then heated to a temperatureof 80°C with stirring for 16 hours. To the reaction solution wasthen added 20 ml of water to terminate the reaction. The resultingorganic phase was washed twice with 20 ml of water, and thendehydrated and dried over anhydrous sodium sulfate. The productwas purified through silica gel column chromatography(hexane/dichloromethane = 6/4), and then recrystallized fromethanol to obtain 14.6 g of 5-fluoro-6-cyano-2-(trans-4-propylcyclohexyl)naphthalene.
    [0110] The following compounds were prepared in the same manneras mentioned above. 5-fluoro-6-cyano-2- (trans-4-ethylcyclohexyl)naphthalene 5-fluoro-6-cyano-2-(trans-4-butylcyclohexyl)naphthalene 5-fluoro-6-cyano-2-(trans-4-pentylcyclohexyl)naphthalene 5-fluoro-6-cyano-2- (trans-4-hexylcyclohexyl)naphthalene 5-fluoro-6-cyano-2- (trans-4-heptylcyclohexyl)naphthalene
    [0111] 10 g of 2-(4-carbamoyl-3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene(synthesized by lithioating 1-fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthaleneobtained in Example 5 with butyllithium, blowing carbon dioxide through the material to producebenzoic acid, reacting the product with thionyl chloride toproduce acid chloride, and then blowing ammonia gas through thematerial) was dissolved in 40 ml of DMF. To the solution was thenadded 2.5 ml of phosphorus oxychloride. The reaction mixture wasthen allowed to undergo reaction at a temperature of 25°C for 2hours. The reaction solution was then poured into ice water. Tothe reaction solution was then added diluted hydrochloric acid.The resulting aqueous phase was then extracted with toluene. Thematerial thus extracted and the organic phase were together washedwith water, saturated aqueous solution of sodium bicarbonate andsaturated brine, and then dehydrated and dried over anhydroussodium sulfate. The residue was purified through silica gelcolumn chromatography (hexane/dichloromethane = 6/4), and thenrecrystallized from ethanol to obtain 7.4 g of 1-fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene.
    [0112] The following compounds were prepared in the same manneras mentioned above. 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl) -6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene
    [0113] To 25.0 g of 6-bromo-2-naphthol and 22.0 g of 3,4-difluorophenylboricacid were added 100 ml of toluene, 50 ml ofethanol, 50 ml of a 2 N aqueous solution of potassium carbonateand 1.3 g of tetrakis(triphenylphosphine)palladium (0). Thereaction mixture was heated under reflux for 3 hours. Thereaction solution was then allowed to cool to room temperature.The resulting organic phase was separated, washed with water andsaturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was purifiedthrough silica gel column chromatography (dichloromethane) toobtain 25.3 g of 6- (3,4-difluorophenyl)-2-naphthol. (12-b) Synthesis of 6-(3,4-difluorophenyl)-2-naphthyltrifluoromethanesulfonate
    [0114] 7.6 g of 6-(3,4-difluorophenyl)-2-naphthol was dissolvedin 30 ml of pyridine. The solution was then cooled to atemperature of not higher than 10°C with ice. To the reactionsolution was then added dropwise 10.0 g oftrifluoromethanesulfonic anhydride at a rate such that thetemperature thereof was kept at 10°C with stirring. The reactionsolution was then returned to room temperature. The reactionsolution was then stirred for 1 hour. To the reaction solutionwas then added 50 ml of water. The reaction solution was extractedwith 100 ml of dichloromothane, washed with water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solventwas then distilled off to obtain 11.4 g of 6-(3,4-difluorophenyl)-2-naphthyl trifluoromethanesulfonate. (12-c) Synthesis of 2-(3,4-difluorophenyl)-6-(1-propynyl)naphthalene
    [0115] 11.4 g of 6-(3,4-difluorophenyl)-2-naphthyltrifluoromethanesulfonate and 60 ml of DMF were dissolved in 20ml of triethylamine. To the solution were then added 0.4 g oftetrakis(triphenylphosphine)palladium (0) and 0.1 g of copper iodide (I). Methyl acetylene was then introduced into thereaction mixture at ordinary temperature and pressure. Thereaction mixture was then stirred for 2 hours. The reactionsolution was neutralized with a 10% hydrochloric acid, extractedwith 100 ml of toluene, and then washed with water and saturatedbrine. The solvent was then distilled off. The residue was thenpurified through silica gel column chromatography (hexane) toobtain 7.4 g of 2-(3,4-difluorophenyl)-6-(1-propinyl)naphthalene. (12-d) Synthesis of 2-(3,4-difluorophenyl)-6-propylnaphthalene
    [0116] 7.4 g of 2-(3,4-difluorophenyl)-6-(1-propynyl)naphthalene was dissolved in 80 ml of ethyl acetate. Tothe solution was then added 1.5 g of 5% palladium carbon. Hydrogenwas then introduced into the reaction mixture at ordinarytemperature and pressure. The reaction mixture was then stirredfor 6 hours. The catalyst was then removed by filtration. Thesolvent was then distilled off to obtain 7.2 g of 2-(3,4-difluorophenyl)-6-propylnaphthalene.The product was thenrecrystallized from methanol to obtain 4.2 g of a purified product.(Cr 62.5 I) (EXAMPLE 13) Synthesis of 2-(3,4,5-trifluorophenyl)-6-propylnaphthalene
    [0117] The procedure of Example 12 was followed except that3,4,5-trifluorophenylboric acid was used instead of 3,4-difluorophenylboricacid to prepare 7 g of 2-(3,4,5-trifluorophenyl)-6-propylnaphthalene from 7 g of 6-bromo-2-naphthol.(Cr 50 I)
    [0118] The following compounds were prepared in the same manneras Examples 12 and 13. 2-(3,4-Difluorophenyl)-6-ethylnaphthalene 2-(3,4-Difluorophenyl)-6-butylnaphthalene 2-(3,4-Difluorophenyl)-6-pentylnaphthalene 2- (3,4-Difluorophenyl)-6-hexylnaphthalene 2- (3,4-Difluorophenyl)-6-heptylnaphthalene 2-(3,4-Difluorophenyl)-6-(3-butenyl)naphthalene 2- (3,4,5-Trifluorophenyl)-6-ethylnaphthalene 2- (3,4,5-Trifluorophenyl) -6-propylnaphthalene 2-(3,4,5-Trifluorophenyl)-6-butylnaphthalene 2-(3,4,5-Trifluorophenyl)-6-pentylnaphthalene 2-(3,4,5-Trifluorophenyl)-6-hexylnaphthalene 2-(3,4,5-Trifluorophenyl)-6-heptylnaphthalene 2-(3,4,5-Trifluorophenyl)-6-(3-butenyl)naphthalene 2-(4-Fluorophenyl)-6-ethylnaphthalene 2-(4-Fluorophenyl)-6-propylnaphthalene 2-(4-Fluorophenyl)-6-butylnaphthalene 2-(4-Fluorophenyl)-6-pentylnaphthalene 2-(4-Fluorophenyl)-6-hexylnaphthalene 2-(4-Fluorophenyl)-6-heptylnaphthalene 2-(4-Fluorophenyl)-6-(3-butenyl)naphthalene 2-(3-Fluorophenyl)-6-ethylnaphthalene 2-(3-Fluorophenyl)-6-propylnaphthalene 2-(3-Fluorophenyl)-6-butylnaphthalene 2-(3-Fluorophenyl)-6-pentylnaphthalene 2-(3-Fluorophenyl)-6-hexylnaphthalene 2-(3-Fluorophenyl)-6-heptylnaphthalene 2-(3-Fluorophenyl)-6- (3-butenyl)naphthalene 2-(3,5-Difluorophenyl)-6-ethylnaphthalene 2-(3,5-Difluorophenyl)-6-propylnaphthalene 2-(3,5-Difluorophenyl)-6-butylnaphthalene 2-(3,5-Difluorophenyl)-6-pentylnaphthalene 2-(3,5-Difluorophenyl)-6-hexylnaphthalene 2-(3,5-Difluorophenyl)-6-heptylnaphthalene 2-(3,5-Difluorophenyl)-6-(3-butenyl)naphthalene 2-Phenyl-6-ethylnaphthalene 2-Phenyl-6-propylnaphthalene 2-Phenyl-6-butylnaphthalene 2-Phenyl-6-pentylnaphthalene 2-Phenyl-6-hexylnaphthalene 2-Phenyl-6-heptylnaphthalene 2-Phenyl-6-(3-butenyl)naphthalene 2-(4-Chlorophenyl)-6-ethylnaphthalene 2-(4-Chlorophenyl)-6-propylnaphthalene 2-(4-Chlorophenyl)-6-butylnaphthalene 2-(4-Chlorophenyl)-6-pentylnaphthalene 2-(4-Chlorophenyl)-6-hexylnaphthalene 2- (4-Chlorophenyl) -6-heptylnaphthalene 2-(4-Chlorophenyl)-6-(3-butenyl)naphthalene 2-(3-Fluoro-4-chlorophenyl)-6-ethylnaphthalene 2-(3-Fluoro-4-chlorophenyl)-6-propylnaphthalene 2-(3-Fluoro-4-chlorophenyl) -6-butylnaphthalene 2-(3-Fluoro-4-chlorophenyl) -6-pentylnaphthalene 2- (3-Fluoro-4-chlorophenyl) -6-hexylnaphthalene 2- (3-Fluoro-4-chlorophenyl) -6-heptylnaphthalene 2-(3-Fluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene 2-(3,5-Difluoro-4-chlorophenyl)-6-ethylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl) -6-propylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl)-6-butylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl)-6-pentylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl) -6-hexylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl) -6-heptylnaphthalene 2-(3,5-Difluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene 2-(4-Trifluoromethoxyphenyl)-6-ethylnaphthalene 2-(4-Trifluoromethoxyphenyl)-6-propylnaphthalene 2-(4-Trifluoromethoxyphenyl)-6-butylnaphthalene 2- (4-Trifluoromethoxyphenyl) -6-pentylnaphthalene 2-(4-Trifluoromethoxyphenyl)-6-hexylnaphthalene 2-(4-Trifluoromethoxyphenyl)-6-heptylnaphthalene 2- (4-Trifluoromethoxyphenyl) -6- (3-butenyl) naphthalene 2-(3-Fluoro-4-trifluoromethoxyphenyl) -6-ethylnaphthalene 2- (3-Fluoro-4-trifluoromethoxyphenyl) -6-propylnaphthalene 2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene 2- (3-Fluoro-4-trifluoromethoxyphenyl) -6-pentylnaphthalene 2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene 2- (3-Fluoro-4-trifluoromethoxyphenyl) -6-heptylnaphthalene 2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene 2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene 2-(3,5-Difluoro-4-trifluoromethoxyphenyl) -6-propylnaphthalene 2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene 2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene 2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene 2- (3,5-Difluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene 2- (3,5-Difluoro-4-trifluoromethoxyphenyl) -6- (3-butenyl)naphthalene 2-(4-Difluoromethoxyphenyl)-6-ethylnaphthalene 2-(4-Difluoromethoxyphenyl)-6-propylnaphthalene 2-(4-Difluoromethoxyphenyl)-6-butylnaphthalene 2-(4-Difluoromethoxyphenyl)-5-pentylnaphthalene 2-(4-Difluoromethoxyphenyl)-6-hexylnaphthalene 2-(4-Difluoromethoxyphenyl)-6-heptylnaphthalene 2-(4-Difluoromethoxyphenyl)-6-(3-butenyl)naphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene 2-(3-Fluoro-4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene 2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene 2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene 2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene 2- (3,5-Difluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene 2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene 2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene 2- (3,5-Difluoro-4-difluoromethoxyphenyl) -6- (3-butenyl) naphthalene 2-[4- (3,4-Difluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,4-Difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-propylnaphthalene 2- [4-(3,4,5-Trifluorophenyl) phenyl] -6-butylnaphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Fluorophenyl)phenyl]-6-heptylnaphthalene 2- [4- (4-Fluorophenyl)phenyl] -6- (3-butenyl) naphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3-Fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,5-Difluorophenyl) phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluorophenyl) phenyl]-6-(3-butenyl) naphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-hexylnaphthalene 2- [4-(4-Chlorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(4-Chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2- [4- (3,5-Difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2- [4- (4-Trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2- [4-(4-Trifluoromethoxyphenyl)phenyl]-6- (3-butenyl)naphthalene 2-[4- (3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2- [4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl] -6-hexylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4- (4-Difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[4- (4-Difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2- [4- (3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl)-6-hexylnaphthalene 2- [4- (3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4- (3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[4-(4-Trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3-Fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Methoxyphenyl)phenyl]-6-heptylnaphthalene 2- [4-(4-Methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[4- (3-Fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2- [4- (3-Fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalone 2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2- [4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2- [4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Allyloxyphenyl)phenyl]-6-heptylnaphthalene 2-[4- (4-Allyloxyphenyl) phenyl] -6- (3-butenyl)naphthalene 2-[4-(4-Methylphenyl)phenyl]-6-ethylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-propylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-butylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-pentylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-hexylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-heptylnaphthalene 2-[4-(4-Methylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-ethylnaphthalene .2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-propylnaphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-butylnaphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-pentylnaphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-hexylnaphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-heptylnaphthalene 2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene 2- [3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene 2- [3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4- (4-fluorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene 2- [3-Fluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4- (3-fluorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4- (4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4- (4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4- (3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4- (4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2- [3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4- (4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene 2- [3-Fluoro-4- (3-fluoro-4-trifluoromethylphenyl)phenyl] -6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2- [3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2- [3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene 2-[3-Fluoro-4- (4-methylphenyl)phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene 2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2- [3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene 2- [3,5-Difluoro-4-(3,4,5-trifluorophenyl) phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl) phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl) phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4- (3-fluorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4- (3-fluorophenyl)phenyl]-6-heacylnaphthalene 2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4- (4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene 2- [3,5-Difluoro-4- (4-chlorophenyl)phenyl]-6- (3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2- [3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4- (3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4- (3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene 2- [3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl) phenyl] -6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl]phenyl]-6-butylnaphthalene 2- [3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4- (3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2- [3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2- [3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2- [3, 5-Difluoro-4- (4-difluoromethoxyphenyl)phenyl] -6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4- (3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4- (4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl) phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4- (4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene 2- [3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4- (4-methylphenyl)phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene 2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene 2- [3,5-Difluoro-4- (4-methylphenyl)phenyl] -6-hexylnaphthalene 2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene 2-[3,5-Difluoro-4-(4-methylphenyl)phenyl-6-(3-butenyl)naphthalene 2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene 2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene 2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene 2- [3,5-Difluoro-4- [4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene 2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene 2- [3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene 2- [3,5-Difluoro-4-(4-(3-butenyl) phenyl]phenyl]-6-(3-butenyl)naphthalene
    [0119] 3.38 g of 6-fluoro-2-bromonaphthalene (synthesized byconverting 6-bromo-2-naphthylamine to a diazonium salt oftetrafluoroboric acid, and then subjecting the diazonium salt tothermal decomposition) was dissolved in 30 ml of tetrahydrofuran(THF), and then cooled to a temperature of -40°C under a nitrogenatmosphere. To the reaction solution was then added dropwise 10ml of n-butyl lithium (1.5 M hexane solution) in 5 minutes. Thereaction mixture was then further stirred. The reaction solutionwas then returned to room temperature. To the reaction solutionwas then added dropwise a solution of 2.20 g of 4-propylcyclohexanonein 10 ml of THF in 5 minutes. The reactionmixture was then stirred for 1 hour. To the reaction solutionwere then added water and a small amount of diluted hydrochloric acid. The reaction solution was extracted with 50 ml of toluene,washed with water and then with saturated brine, and thendehydrated and dried over anhydrous sodium sulfate. To theresidue was then added 300 mg of p-toluenesulfonic acidmonohydrate. The reaction mixture was then heated under refluxwhile the azeotropically distilled water was being driven out ofthe system for 2 hours. The reaction solution was allowed to cool,washed sequentially with water, saturated aqueous solution ofsodium bicarbonate, water and saturated brine, and thendehydrated and dried over anhydrous sodium sulfate. The solventwas distilled off to obtain a crude crystal which was then purifiedthrough silica gel column chromatography (hexane) to obtain 2.1 Ng of 6-fluoro-2- (4-Fropylcyclohexenyl)naphthalene in the form ofwhite crystal. The total amount of 6-fluoro-2-(4-propylcyclohexenyl)naphthalenewas dissolved in 20 ml of ethylacetate. To the solution was then added 200 mg of 5% palladiumcarbon. The reaction mixture was then stirred at a hydrogenpressure of 4 atm for 5 hours. The catalyst was then removed byfiltration through Celite. The solvent was then distilled offto obtain 2.1 g of 6-fluoro-2- (4-propylcyclohexyl) naphthalene inthe form of crude product (cis/trans mixture) . The crude productwas then dissolved in 20 ml of N,N-dimethylformamide (DMF). Tothe reaction mixture was then added 400 mg of potassium t-butoxide.The reaction mixture was then stirred at a temperature of from 40°C to 50°C for 1 hour. To the reaction mixture were then addedhexane and water. The reaction mixture was then treated withdiluted hydrochloric acid to become weakly acidic. The resultinghexane phase was then separated. The resulting aqueous phase wasthen extracted with hexane. The material thus extracted and thehexane phase were together washed with water and saturated brine.The solvent was then distilled off. The residue was purifiedthrough silica gel column chromatography (hexane), and thenrecrystallized twice from ethanol to obtain 0.75 g of 6-fluoro-2-(trans-4-propylcyclohexyl)naphthalenein the form ofwhite crystal. (EXAMPLE 15) Synthesis of 5,6-difluoro-2-(trans-4-pentylcyclohexyl)naphthalene
    [0120] The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene (synthesized by converting 6-bromo-1-fluoro-2-naphthylamineto a diazonium salt oftetrafluoroboric acid, and then subjecting the diazonium salt tothermal decomposition) was used instead of 6-fluoro-2-bromonaphthaleneand 4-pentylcyclohexanone was used instead of4-propylcyclohexanone to obtain 5,6-difluoro-2-(trans-4-pentylcyclohexyl)naphthalene.
    [0121] The following compounds were prepared in the same manneras mentioned above. 6-Fluoro-2-(trans-4-pentylcyclohexyl)naphthalene 6-Fluoro-2-(trans-4-heptylcyclohexyl)naphthalene 6-Fluoro-2-(trans-4-methoxymethylcyclohexyl) naphthalene 5,6-Difluoro-2-(trans-4-propylcyclohexyl)naphthalene 5,6-Difluoro-2-(trans-4-heptylcyclohexyl)naphthalene 5,6,7-Trifluoro-2-(trans-4-propylcyclohexyl)naphthalene 5,6,7-Trifluoro-2-(trans-4-pentylcyclohexyl)naphthalene 5,6,7-Trifluoro-2-(trans-4-heptylcyclohexyl)naphthalene 6-Fluoro-2-(trans-4'-ethylbicyclohexane-trans-4-yl)naphthalene 6-Fluoro-2-(trans-4'-propylbicyclohexane-trans-4-yl)naphthalene 6-Fluoro-2-(trans-4'-butylbicyclohexane-trans-4-yl)naphthalene 6-Fluoro-2-(trans-4'-pentylbicyclohexane-trans-4-yl)naphthalene 5,6-Difluoro-2-(trans-4'-ethylbicyclohexane-trans-4-yl)naphthalene 5,6-Difluoro-2-(trans-4'-propylbicyclohexane-trans-4-yl)naphthalene 5,6-Difluoro-2-(trans-4'-butylbicyclohexane-trans-4-yl)naphthalene 5,6-Difluoro-2-(trans-4'-pentylbicyclohexane-trans-4-yl)naphthalene 5,6,7-Trifluoro-2-(trans-4'-ethylbicyclohexane-trans-4-yl)naphthalene 5,6,7-Trifluoro-2-(trans-4'-propylbicyclohexane-trans-4-yl)naphthalene 5,6,7-Trifluoro-2- (trans-4'-butylbicyclohexane-trans-4-yl)naphthalene 5,6,7-Trifluoro-2-(trans-4'-pentylbicyclohexane-trans-4-yl)naphthalene 4,5,6,7-Tetrafluoro-2-(trans-4'-ethylbicyclohexane-trans-4-yl)naphthalene 4,5,6,7-Tetrafluoro-2-(trans-4'-propylbicyclohexane-trans-4-yl)naphthalene 4,5,6,7-Tetrafluoro-2-(trans-4'-butylbicyclohexane-trans-4-yl)naphthalene 4,5,6,7-Tetrafluoro-2-(trans-4'-pentylbicyclohexane-trans-4-yl)naphthalene 6-Fluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene 6-Fluoro-2- [trans-4- [2- (trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 6-Fluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene 6-Fluoro-2-[trans-4-[2- (trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6-Difluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6-Difluoro-2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6-Difluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6-Difluoro-2-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene 5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene
    [0122] The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene was used instead of 6-fluoro-2-bromonaphthalene,4-propylcyclohexaneethanal was used insteadof 4-propylcyclohexanone and isomerization with potassium t-butoxidewas not effected to obtain 5,6-difluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene.
    [0123] The following compounds were prepared in the same manneras mentioned above. 5,6-Difluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 5,6-Difluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4'-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4'-propylbicyclohexane-trans-4-yl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4'-butylbicyclohexane-trans-4-yl)ethyl]naphthalene 6-Fluoro-2-[2-(trans-4'-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6-Difluoro-2-[2-(trans-4'-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6-Difluoro-2-[2-(trans-4'-propylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6-Difluoro-2-[2-(trans-4'-butylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6-Difluoro-2-[2-(trans-4'-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4'-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4'-propylbicyclohexane-trans-4-yl)ethyl]naphthalene(I-5) 5,6,7-Trifluoro-2-[2-(trans-4'-butylbicyclohexane-trans-4-yl)ethyl]naphthalene 5,6,7-Trifluoro-2-[2-(trans-4'-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene 6-Fluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 6-Fluoro-2-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 5,6-Difluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 5,6-Difluoro-2-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 5,6,7-Trifluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 5,6,7-Trifluoro-2-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 6-Fluoro-2-[2-[2-6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 6-Fluoro-2-[2-[2-6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 5,6-Difluoro-2-[2-[2-6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 5,6-Difluoro-2-[2-[2-6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 5,6,7-Trifluoro-2-[2-[2-6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 5,6,7-Trifluoro-2-[2-[2-6-difluoro-4- (trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene
    [0124] The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene was used instead of 6-fluoro-2-bromonaphthaleneand bicyclohexane-4,4'-dionemonoethyleneacetalwas used instead of 4-propylcyclohexanone.The foregoing procedure was followed by deacetalation with formic acid to obtain trans-4'-(5,6-difluoronaphthyl)bicyclohexane-4-one.Separately, a Wittigreagent was prepared from methoxymethyltriphenylphosphoniumchloride and potassium t-butoxide in THF under cooling with ice.To the Wittig reagent was then added dropwise a solution of theforegoing trans-4'-(5,6-difluoronaphthyl)bicyclohexane-4-oneat a temperature of 0°C. After 1 hour of reaction, the reactionsolution was then returned to room temperature. To the reactionsolution was then added water. The resulting organic phase wasthen concentrated. To the organic phase was then added hexaneto make a solution. Insoluble triphenylphosphine oxide was thenremoved by filtration. The residue was then washed with a 1/1mixture of methanol and water. The resulting hexane phase wasthen concentrated to obtain a crude product. The crude productwas then dissolved in ethanol. To the solution was then addedan ethanol solution of potassium hydroxide. The reaction mixturewas then stirred at room temperature for 1 hour. To the reactionsolution was then added water. The reaction solution wasneutralized with diluted hydrochloric acid, and then neutralizedwith toluene. The resulting organic phase was washed with water,and then dehydrated and dried over anhydrous sodium sulfate. Thesolvent was then distilled off to obtain trans-4'-(5,6-difluoronaphthyl)bicyclohexane-trans-4-carbaldehydein crystalform. The crystal was then reacted with a Wittig reagent prepared from methoxymethyltriphenylphosphonium iodide and potassiumt-butoxide to obtain 5,6-difluoro-2-(trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene.
    [0125] The following compounds were prepared in the same manneras mentioned above. 5,6-Difluoro-2-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 6-Fluoro-2- (trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 6-Fluoro-2- [trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 5,6,7-Trifluoro-2-(trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 5,6,7-Trifluoro-2-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 4,5,6,7-Tetrafluoro-2- (trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 4,5,6,7-Tetrafluoro-2-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 6-Fluoro-2-(trans-4-vinylcyclohoxyl) naphthalene 6-Fluoro-2-[trans-4-(3-butenyl)cyclohexyl]naphthalene 5,6-Difluoro-2-(trans-4-vinylcyclohexyl)naphthalene 5, 6-Difluoro-2-[trans-4-(3-butenyl) cyclohexyl]naphthalene 5,6,7-Trifluoro-2-(trans-4-vinylcyclohexyl)naphthalene 5, 6,7-Trifluoro-2-[trans-4-(3-butenyl)cyclohexyl]naphthalene
    [0126] To a THF solution of an organic lithium reagent preparedfrom 5,6-difluoro-2-bromonaphthalene were added dropwise 4-iodo-1-(trans-4-propylcyclohexyl)benzeneand a THE solution oftetrakis(triphenylphosphine)palladium (0) in the catalyticamount, The reaction mixture was then stirred at room temperaturefor 3 hours. To the reaction mixture were then added water andtoluene to terminate the reaction. To the reaction solution wasthen added diluted hydrochloric acid until the aqueous phasebecame weakly acidic. The reaction solution was then extractedwith toluene. The material thus extracted and the organic phasewere together washed with water and then with saturated brine,and then dried over anhydrous sodium sulfate. The solvent wasdistilled off under reduced pressure to obtain an oily matter.The oily matter was purified through silica gel columnchromatography (hexane), and then recrystallized from ethanol toobtain 5,6-difluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalenein the form of whitecrystal.
    [0127] The following compounds were prepared in the same manneras mentioned above. 5,6-Difluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 6-Fluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 5,6-Difluoro-2-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene
    [0128] 1.5 g of sodium hydride was suspended in 5 ml oftetrahydrofuran (THF) under cooling by an ice-water bath. To thesuspension was then added dropwise 40 ml THF solution of 10.0 gof 1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-ol(obtained by reacting a Grignard reagent prepared from 6-bromo-2-methoxynaphthaleneand magnesium with 4-propylcyclohexanone,subjecting the product to dehydration in thepresence of an acid to obtain a naphthylcyclohexene derivative,subjecting the naphthylcyclohexene derivative to catalyticreduction, treating the material with a strongly basic potassiumt-butoxide in DMF so that the cyclohexane ring was isomerized totrans form, subjecting the material to demethylation with hydrobromic acid, and then fluorinating the material with N-fluoro-5-trifluoromethoxypyridinium-2-sulfonate).Afterseveral hours of stirring, to the reaction solution was then addeddropwise 30 ml of a THF solution of 7.4 g of S-ethylchlorodithiocarbonate. After 1 hour of stirring, to the reactionsolution was then added 20 ml of water to terminate the reaction.To the reaction solution was then added 50 ml of ethyl acetate.The organic phase was further washed twice with 20 ml of water,and then dehydrated and dried over anhydrous sodium sulfate.Subsequently, the solvent was distilled off under reducedpressure to obtain 12.0 g of S-ethyl-O-1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate, 12.0 g ofS-ethyl-O-1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate thus obtained was dissolved in 48 ml ofdichloromethane, and then added dropwise to 1 literdichloromethane solution of 300 g of hydrogen fluoride-melaminecomplex and 1,3-dibromo-5,5-dimethylhydantoin which had beencooled to a temperature of 0 °C. After 30 minutes of stirring,to the reaction solution was then added 200 ml of water to terminatethe reaction. The resulting organic phase was washed twice with200 ml of water, and then dehydrated and dried over anhydroussodium sulfate. The solvent was then distilled off. The residuewas then purified through silica gel column chromatography(developing solvent: hexane). The total amount of the purified product was then dissolved in 50 ml of THF. To the solution wasthen added dropwise 43 ml of a 1.6 M hexane solution of butyllithium at a temperature of -78 °C. After the termination ofdropwise addition, the reaction mixture was then stirred for 10minutes. To the reaction mixture was then added 10 ml of water.The reaction mixture was then returned to room temperature. Tothe reaction mixture was then added 20 ml of water. The resultingorganic phase was washed twice with 20 ml of water, and thendehydrated and dried over anhydrous sodium sulfate. The productwas purified through silica gel column chromatography(hexane/ethyl acetate = 9/1), and then recrystallized fromethanol to obtain 7.1 g of 5-fluoro-5-trifluoromethoxy-2-(trans-4-propylcyclohexyl)naphthalene. (EXAMPLE 20) Synthesis of 1,3-difluoro-2-trifluoromethoxy-6-(trans-4-propylcyclohexyl)naphthalene
    [0129] The procedure of Example 19 was followed except that1,3-difluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-ol(obtained by reacting a Grignard reagent prepared from 1,3-difluoro-6-bromo-2-methoxynaphthalenewith 4-propylcyclohexanone, subjecting the product to dehydration in thepresence of an acid to obtain a naphthylcyclohexene derivative,subjecting the naphthylcyclohexene derivative to catalyticreduction, treating the material with a strongly basic potassium t-butoxide in DMF so that the cyclohexane ring was isomerized totrans form, and then subjecting the material to demethylation withhydrobromic acid) was used instead of 1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-olto produce S-ethyl-O-1,3-difluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate. The product was then similarlytrifluoromethoxylated to obtain 5,7-difluoro-6-trifluoromethoxy-2-(trans-4-propylcyclohexyl)naphthalene.
    [0130] The following compounds were prepared in the same manneras in Example 19 or 20. 2-Trifluoromethoxy-6-(trans-4-propylcyclohexyl)naphthalene 2-Trifluoromethoxy-6-(trans-4-butylcyclohexy)naphthalene 2-Trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(trans-4-butylcyclohexyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-butylcyclohexyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene trans-4'-Ethyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Propyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Pentyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Ethyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Propyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Pentyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Ethyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Propyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Pentyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Ethyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Propyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane trans-4'-Pentyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane 2-Trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 2-Trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene
    [0131] The procedure of Example 20 was followed except that1-fluoro-6-bromo-2-methoxynapthalene was used instead of 1,3-difluoro-6-bromo-2-methoxynaphthalene,4-propylcyclohexaneethanal was used instead of 4-propylcyclohexanone andisomerization with potassium t-butoxide was not effected toobtain 1-fluoro-2-trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene.
    [0132] The following compounds were prepared in the same manneras mentioned above. 2-Trifluoromethoxy-6- [2- (trans-4-propylcyclohexyl)ethyl]naphthalene 2-Trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene Trans-4'-propyl-trans-4-[2-(2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane Trans-4' -pentyl-trans-4-[2-(2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane Trans-4'-propyl-trans-4-[2-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane Trans-4'-pentyl-trans-4-[2-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane Trans-4'-propyl-trans-4-(2-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane Trans-4'-pentyl-trans-4-[2-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane 2-Trifluoromethoxy-6-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 2-Trifluoromethoxy-6-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 2-Trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 2-Trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene
    [0133] A Wittig reagent was prepared from methoxymethyltriphenyl phosphonium chloride and potassium t-butoxide in THFunder cooling with ice. To the Wittig reagent was then added aTHF solution of trans-4'-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)bicyclohexane-4-one(obtained by reacting a Grignard reagent prepared from 1-fluoro-6-bromo-2-trifluoromethoxynaphthalenewithbicyclohexanone-4,4'-dionemonoethyleneacetal, subjecting theproduct to dehydration in the same manner as mentioned above,subjecting the product to catalytic reduction, and then deacetalating the product with formic acid) at a temperature of0°C. After 1 hour of reaction, the reaction solution was returnedto room temperature. The reaction solution was then added water.The resulting organic phase was then concentrated. To thematerial thus concentrated was then added hexane to make asolution. Insoluble triphenylphosphine oxide was then removedby filtration. The filtrate was then washed with a 1/1 mixtureof methanol and water. The resulting hexane phase wasconcentrated to obtain a crude product which was then dissolvedin ethanol. To the solution was then added an ethanol solutionof potassium hydroxide. The reaction mixture was then stirredat room temperature for 1 hour. To the reaction solution was thenadded water. The reaction solution was neutralized with dilutedhydrochloric acid, and then extracted with toluene. Theresulting organic phase was washed with water, and then dehydratedand dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain trans-4'-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)bicyclohexane-trans-4-carbaldehydein crystal form. The crystal thus obtained was thenreacted with a Wittig prepared from methoxymethyl triphenylphosphonium iodide and potassium t-butoxide to obtain 1-fluoro-2-trifluoromethoxy-6-(trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene.
    [0134] The following compounds were prepared in the same manner as mentioned above. 2-Trifluoromethoxy-6- (trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 2-Trifluoromethoxy-6-[trans-4'-(3-butenyl)bicyclohexane6-trans-4-yl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl] naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-(trans-4'-vinylbicyclohexane-trans-4-yl)naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[trans-4'-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene 2-Trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene 2-Trifluoromethoxy-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene
    [0135] 3,4 g of 4-propylphenylboric acid (obtained by reactinga Grignard reagent prepared from, 1-bromo-4-propylbenzene withtrimethyl borate, and then subjecting the product to hydrolysiswith hydrochloric acid) and 25.5 g of 6-bromo-2-naphthol weredissolved in a mixture of 92 ml of toluene, 46 ml of ethanol and92 ml of water. To the solution ware then added 25.5 g of potassiumcarbonate and 1.3 g of tetrakis (triphenyl phoephine)palladium (0).The reaction mixture was then stirred at a temperature of 75 °Cfor 7 hours. To the reaction solution were then added water andtoluene. To the reaction solution was then added dilutedhydrochloric acid until the aqueous phase became weakly acidic.The reaction solution was then extracted with toluene. Thematerial thus extracted and the organic phase were together washedwith water and then with saturated brine, and then dried overanhydrous sodium sulfate. The solvent was then distilled offunder reduced pressure to obtain 41.4 g of 6-(4-propylphenyl)naphthalene-2-ol.12.7 g of 6-(4-propylphenyl)naphthalene-2-olwas then dissolved in 50 ml ofdichloromethane. To the solution was then added 13.1 g of N-fluoro-5-trifluoromethoxypyridinium-2-sulfonate. Thereaction mixture was then stirred at room temperature for 18 hours.The reaction mixture was post-treated in the same manner asmentioned above to obtain an oily matter which was then purifiedthrough silica gel column chromatography (hexane/ethyl acetate= 9/1) to obtain 10 g of 1-fluoro-6-(4-propylphenyl)naphthalene-2-ol.The product was converted toS-ethyl dithiocarbonate which was then trifluoromethoxylated inthe same manner as in Example 1-to obtain 2.3 g of the titled1-fluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene. (EXAMPLE 24) Synthesis of 1,3-difluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene
    [0136] 7.3 g of 4-propylphenylboric acid and 11 g of 1,3-difluoro-2-trifluoromethoxynaphthalene-6-yltrifluoromethanesulfonate (obtained by triflating 1,3-difluoro-2-trifluoromethoxynaphthalene-6-olwithtrifluoromethanesulfonic anhydride) were dissolved in 50 ml ofDMF. To the solution was then added 0.4 g oftetrakis (triphenylphosphine)palladium (0). The reactionmixture was stirred at a temperature of 85 °C for 8 hours. Tothe reaction solution were then added water and toluene. Theresulting aqueous phase was then extracted with toluene. Thematerial thus extracted and the organic phase were together washed with water and then with saturated brine, and then dried overanhydrous sodium sulfate. The solvent was then distilled offunder reduced pressure to obtain an oily matter. The oily matterthus obtained was purified through silica gel columnchromatography (hexane/ethyl acetate = 9/1), and thenrecrystallized from ethanol to obtain 6.3 g of 1,3-difluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalenein crystalform. (EXAMPLE 25) Synthesis of 1-fluoro-2-trifluoromethoxy-6- (2-fluoro-4-propylphenyl)naphthalene
    [0137] The procedure of Example 23 was followed except that2-fluoro-4-propylphonylboric acid was used instead of 4-propylphenylboricacid to obtain 1-fluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene.
    [0138] The following compounds were prepared in the same manneras in Example 23, 24 or 25. 2-Trifluoromethoxy-6-(4-propylphenyl)naphthalene 2-Trifluoromethoxy-6-(4-pentylphenyl)naphthalene 2-Trifluoromethoxy-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6- (4-pentylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-pentylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4- (3-butenyl)phenyl]naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-(4-pentylphenyl)naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]naphthalene 2-Trifluoromethoxy-6- (2-fluoro-4-propylphenyl)naphthalene 2-Trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)naphthalene 2-Trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene 2-Trifluoromethoxy-6- [2-fluoro-4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]naphthalene 2-Trifluoromethoxy-6-(2-6-difluoro-4-propylphenyl)naphthalene 2-Trifluoromethoxy-6-(2-6-difluoro-4-pentylphenyl)naphthalene 2-Trifluoromethoxy-6-(2-6-difluoro-4-heptylphenyl)naphthalene 2-Trifluoromethoxy-6-[2-6-difluoro-4-(3-butenyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-propylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-pentylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-heptylphenyl)naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-6-difluoro-4-(3-butenyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6- (2-fluoro-4-pentylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-heptylphenyl)naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6- [4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6- [2,6-difluoro-4- (trans-4-propylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene 2-Trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 2-Trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 2-Trifluoromethoxy-6- [2,6-difluoro-4- [2- (trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene 4'-Ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Butyl-4- (2-trifluoromethoxynaphthalene-6-yl) biphenyl 4'-Pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-(3-Butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Ethyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Propyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Butyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-Pentyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-(3-Butenyl) -4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-ethyl-4-(1,3-Difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-pentyl-4- (1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 4'-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-butyl-4- (2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-(3-butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-ethyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-propyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-butyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-pentyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-(3-butenyl)-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 2'-Fluoro-4'-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-butyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-(3-butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-ethyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-propyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'--butyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-pentyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-(3-butenyl)-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3,5-Difluoro-4'-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-ethyl4- (6-trifluoromethoxynaphthalene-2-yl)biphenyl 3-Fluoro-4'-propyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl 3-Fluoro-4'-butyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl 3-Fluoro-4'-pentyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl 3-Fluoro-4'-(3-butenyl) -4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl 3-Fluoro-4'-ethyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-propyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-butyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-pentyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-(3-butenyl)-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl 3-Fluoro-4'-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl
    [0139] 10 g of 4-propyl-1-ethynylbenzene and 19.5 g of 2-broma-5-fluoro-6-trifluoromethoxynaphthalenewere dissolved in50 ml of N,N-dimethylformamide (DMF). To the solution were thenadded 50 mg of copper iodide (I) and 100 mg oftetrakis(triphenylphosphine)palladium (0). The reactionmixture was then stirred at room temperature for 5 hours. To thereaction solution was then added toluene. Insoluble matters wereremoved by filtration. The residue was then washed with waterand saturated brine. The solvent was then distilled off. Theresidue was purified through silica gel column chromatography(hexane/ethyl acetate 9/1), and then recrystallized from ethanolto obtain 8.6 g of 1-fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene.
    [0140] The following compounds were prepared in the same manneras mentioned above. 2-Trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-(4-propylphenyl)ethynylnaphthalene 2 -Trifluoromethoxy-6-(4-butylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-(4-pentylphenyl) ethynylnaphthalene 2-Trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(4-butylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(4-pentylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-propylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-butylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(4-pentylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6- (2-fluoro-4-ethylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6- (2-fluoro-4-butylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6- (2-fluoro-4-pentylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-ethylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-butylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-ethylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-butylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6- (2,6-difluoro-4-propylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6- (2,6-difluoro-4-butylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-butylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-butylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4- (3-butenyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene 2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 2-Trifluoremethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phanyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene 1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene
    [0141] The procedure of Example 9 was followed except that1-fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-propylnaphthalenewas used instead of 1-fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-(trans-4-propyl cyclohexyl)naphthalene to obtain 2-(4-cyanophenyl)-6-propylnaphthalene in the form of white crystal. (EXAMPLE 28) Synthesis of 2-(3-fluoro-4-cyanophenyl)-6-propylnaphthalene
    [0142] The procedure of Example 10 was followed except that1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6-propylnaphthalene wasused instead of 1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthaleneto obtain 2-(3-fluoro-4-cyanophenyl)-6-propylnaphthalenein the form of white crystal. (EXAMPLE 29) Synthesis of 2-(3,5-difluoro-4-cyanophenyl)-6-propylnaphthalene
    [0143] The procedure of Example 11 was followed except that1-fluoro-2-(3,5-difluorophenyl)-6-propylnaphthalene was usedinstead of 1-fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthaleneto obtain 2-(3,5-difluoro-4-cyanophenyl)-6-propylnaphthalenein the form of white crystal.
    [0144] The following compounds were prepared in the same manneras in Examples 27, 28 and 29. 1-Fluoro-2-(4-cyanophenyl)-6-ethylnaphthalene 1-Fluoro-2-(4-cyanophenyl)-6-propylnaphthalene 1-Fluoro-2-(4-cyanophenyl)-6-butylnaphthalene 1-Fluoro-2-(4-cyanophenyl)-6-pentylnaphthalene 1-Fluoro-2-(4-cyanophenyl)-6-hexylnaphthalene 1-Fluoro-2-(4-cyanophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-butylnaphthalene 1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-heptylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-ethylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-butylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-hexylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-heptylnaphthalene 2-(4-cyanophenyl)-6-ethylnaphthalene 2- (4-cyanophenyl)-6-propylnaphthalene 2- (4-cyanophenyl) -6-butylnaphthalene 2-(4-cyanophenyl)-6-pentylnaphthalene 2-(4-cyanophenyl)-6-hexylnaphthalene 2-(4-cyanophenyl)-6-heptylnaphthalene 2-[3-Fluoro-4-cyanophenyl)-6-ethylnaphthalene 2-[3-Fluoro-4-cyanophenyl)-6-butylnaphthalene 2-[3-Fluoro-4-cyanophenyl)-6-pentylnaphthalene 2-[3-Fluoro-4-cyanophenyl)-6-hexylnaphthalene 2-[3-Fluoro-4-cyanophenyl)-6-heptylnaphthalene 2-(3,5-Difluoro-4-cyanophenyl)-6-ethylnaphthalene 2-(3,5-Difluoro-4-cyanophenyl)-6-butylnaphthalene 2-(3,5-Difluoro-4-cyanophenyl)-6-pentylnaphthalene 2-(3,5-Difluoro-4-cyanophenyl)-6-hexylnaphthalene 2-(3,5-Difluoro-4-cyanophenyl)-6-heptylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl)-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl) phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene 1-Fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene 1-Fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene 1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene
    [0145] A general-purpose host liquid crystal (H) having thefollowing structure:
    [0146] For the measurement of threshold voltage (Vth) andresponse, the nematic liquid crystal composition is filled is aTN cell having a thickness of 6 µm. The measurement is effectedat a temperature of 20°C. The term "response" as used herein ismeant to indicate the response time shown during the applicationof voltage at which the rise time (τr) and the drop time (τd) are equal to each other.
    [0147] 80% of the host liquid crystal composition (H) and thecompound represented by the formula (Ib-1) of the presentinvention obtained in Example 15:
    [0148] Subsequently, the nematic liquid crystal composition(M-1) was filled in a TN cell having a thickness of 4.5 µm to preparea liquid crystal device. The liquid crystal device was thenmeasured for electro-optical properties. The results are asfollows: Upper nematic phase temperature limit (TN-1) 98.6°C Dielectric anisotropy (Δε) 4.60 Threshold voltage (Vth) 1.76 V Response (τr = τd) 24.2 m sec.
    [0149] It can thus be seen that the addition of the compound(Ib-1) makes it possible to provide a quick response similarlyto the host liquid crystal composition (H), a lower dielectricanisotropy than the host liquid crystal composition. (H) and athreshold voltage drop of about 10% from that of the host liquidcrystal composition (H). The liquid crystal device thus obtainedwas then measured for voltage holding ratio at room temperatureand 80°C. The results were good at any of the two temperatureranges, demonstrating that the liquid crystal device can besufficiently used in active matrix driving. (EXAMPLE 31) Preparation of liquid crystal composition (2)
    [0150] 80% of the host liquid crystal composition (H) and thecompound (Ib-2) of the present invention obtained in Example 15:
    [0151] It can thus be seen that the compound (Ib-1) exhibits asmaller dielectric anisotropy than the host liquid crystal (H)and a threshold voltage drop of about 20% from the host liquid crystal (H).
    [0152] The nematic liquid crystal composition (M-2) was thensubjected to heat stability test and ultraviolet ray irradiationtest in the same manner as the nematic liquid crystal composition(M-1). As a result, the composition (M-2) showed no change ofTN-1 after these tests. The nematic liquid crystal composition(M-2) was then measured for voltage holding ratio. As a result,the composition (M-2) exhibited a sufficiently high voltageholding ratio during preparation, after heating and afterirradiation with ultraviolet rays.
    [0153] As mentioned above, the compound represented by thegeneral formula (I) is very useful in the preparation of a liquidcrystal composition having (a) a wide nematic phase operatingtemperature range, (b) a threshold voltage low enough to driveat a low voltage, (c) a quick response and (d) a voltage holdingratio high enough active matrix driving. (EXAMPLE 32) Preparation of liquid crystal composition (2)
    [0154] 80% of the host liquid crystal composition (H) and thecompound (Ic-7) of the present invention obtained in Example 2:
    [0155] It can thus be seen that the addition of the compound(Ic-7) makes it possible to raise the upper nematic phasetemperature limit (TN-1) by not lower than 3°. The nematic liquidcrystal composition (M-3) was cooled to a temperature of -60°Cto undergo crystallization. The nematic liquid crystalcomposition (M-3) thus crystallized was than measured for meltingpoint (TC-N). The results were -2°C, demonstrating that thecomposition (M-3) exhibits a malting point drop of as much as 13°from the host liquid crystal composition (H). Accordingly, thestable temperature range of nematic phase can be expanded by as much as about 16°. It can also be seen that the addition of thecompound (Ic-7) makes it possible to increase the dielectricanisotropy of liquid crystal composition and lower the thresholdvoltage of liquid crystal composition. The increase in thebirefringence index could be suppressed to 0.02 from that of thehost liquid crystal (H).
    [0156] The liquid crystal device was then measured for voltageholding ratio at room temperature and 80°C. The results wereextremely good at any of the two temperature ranges, demonstratingthat it can be sufficiently used in active matrix driving. (COMPARATIVE EXAMPLE 1)
    [0157] A compound represented by the following general formula(R-1) having a structure similar to the compound (Ic-7) but having1,4-phenylene group instead of 2,6-naphthylene group:
    [0158] 80% of the host liquid crystal composition (H) and thecompound (Id-1) of the present invention obtained in Example 12:
    [0159] It can thus be seen that the addition of the compound(Id-1) in an amount of 20% causes a slight drop of the upper nematicphase temperature limit (TN-1) but makes it possible to lower thethreshold voltage of the liquid crystal composition anddrastically raise the birefringence index of the liquid crystalcomposition (by about 0.02 from that of the host liquid crystalcomposition (H)) without deteriorating the reaponse.Subsequently, the liquid crystal composition was allowed to standat room temperature for 1 month. However, no crystallization orphase separation were observed. It can thus be seen that thecompound (Id-1) has an excellent miscibility with theconventional liquid crystals. The liquid crystal composition(M-4) was cooled to a temperature of -15°C to undergocrystallization, and then measured for melting point (TC-N). Theresults were 14°C. (EXAMPLE 34) Preparation of liquid crystal composition (5)
    [0160] To 80% of the host liquid crystal composition (H) wasadded the compound represented by the formula (Id-2) of thepresent invention obtained in Example 13:
    [0161] The comparison of the liquid crystal composition (M-5)with the liquid crystal composition (M-4) shows that the liquidcrystal composition (M-5) exhibits a slightly lower TN-1 and aslightly reduced birefringence index but has a quick responsesimilarly to the liquid crystal composition (M-4) and a furtherdrop of threshold voltage. (EXAMPLE 35) Preparation of liquid crystal composition (6)
    [0162] To 80% of the host liquid crystal composition (H) was added the compound represented by formula (Id-7) of the presentinvention obtained in Example 12:
    [0163] The addition of the compound (Id-7) in an amount of 20%causes a slight drop of the upper nematic phase temperature limit(TN-1) but can provide a quick response similarly to the host liquidcrystal composition (H) and makes it possible to drastically lowerthe threshold voltage of the liquid crystal composition (by 0.3V). Further, the birefringence index of the liquid crystal composition can be drastically increased from thehost liquid crystal composition (H). (COMPARATIVE EXAMPLE 2)
    [0164] The procedure of Examples 33 to 35 were followed exceptthat the compound represented by formula (Ic) was replaced by acompound represented by the following formula (R-2) having astructure similar to that of the compound (Ic) but having1,4-phenylene group instead of 2,6-naphthylene group:
    [0165] The comparison of the liquid crystal composition (HR-2)with the liquid crystal composition (H-1) shows that the liquidcrystal composition (HR-2) exhibits a slightly more quickresponse and a slightly lower threshold voltage (Vth). However,the upper nematic phase temperature limit (TN-1) of the liquidcrystal composition (HR-2) showed a further drop. The liquidcrystal composition (HR-2) also showed only a slight increase inbirefringence index.
    [0166] The naphthalene derivative provided by the presentinvention exhibits an excellent liquid-crystallinity andmiscibility with currently widely used liquid crystalcompositions or compositions. The addition of the naphthalenederivative makes it possible to drastically lower the thresholdvoltage of the liquid crystal composition while maintaining itshigh response. The naphthalene derivative of the presentinvention is characterized by a large birefringence index.Further, most or the naphthalene derivative of the presentinvention has no strongly polar group in its molecule and thuscan also be used for active matrix driving. Moreover, as shownin the foregoing examples, the naphthalene derivative of thepresent invention can be easily produced and is colorless andchemically stable. Accordingly, the liquid crystal compositioncomprising the naphthalene derivative of the present invention is extremely useful as a practical liquid crystal composition,particularly a liquid crystal composition which can operatewithin a wide temperature range and requires a high speed responseand a low voltage driving.
    权利要求:
    Claims (20)
    [1] A naphthalene darivative represented by thefollowing general formula (I) :
    [2] The compound according to Claim 1, wherein in thegeneral formula (I) a and b each represent 1.
    [3] The compound according to Claim 1, wherein in thegeneral formula (I) a is 1, b is 0 and Za is a group selected fromthe group consisting of fluorine atom, chlorine atom,trifluoromethoxy group, and C1-20, alkyl, alkoxyl, alkenyl oralkenyloxy group which may be substituted by from 1 to 7 fluorineatoms or or from 1 to 7 fluorine atoms.
    [4] The compound according to Claim 1, wherein in thegeneral formula (I) a is 1, b is 0 and Za is a group representedby the general formula (IIa).
    [5] The compound according to Claim 1, wherein in thegeneral formula (I) a and b each are 0 and Za represents a grouprepresented by the general formula (IIa).
    [6] The compound according to Claim 1, wherein in thegeneral formula (I) a and b each are 0 and Za represents a grouprepresented by the general formula (IIb).
    [7] The compound according to any one of Claims 1 to 6,wherein La, Lb, Lc and Ld in the general formula (I) eachindependently represent a group selected from the group consisting of -CH2CH2- and single bond.
    [8] The compound according to any one of Claims 1 to 4and 7, wherein ring A in the general formula (I) represents a groupselected from the group consisting of trans-1,4-cyclohexylanegroup, 1,4-phenylene group, 2-fluoro-1,4-phenylene group,2,6-difluoro-1,4-phenylene group andtrans¥decahydronaphthalene-2,6-diyl group.
    [9] The compound according to any one of Claims 1, 2, 7and 8, wherein ring B in the general formula (I) represents atrans-1,4-cyclohexylene group.
    [10] The compound according to any one of Claims 1 and4 to 7, wherein rings C and D in the general formula (I) eachindependently represent a group selected from the groupconsisting of 1,4-phenylene group, 2-fluoro-1,4-phenylene group,3-fluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene groupand 3,5-difluoro-1,4-phenylene group.
    [11] The compound according to any one of Claims 1 to 3and 7 to 9, wherein Za in the general formula (I) represents agroup selected from the group consisting of C4-12 alkenyl groupwhich may be substituted by from 1 to 3 fluorine atoms and C3-12alkenyloxy group which may be substituted by from 1 to 3 fluorineatoms.
    [12] The compound according to any one of Claims 1 to 3and 7 to 9, wherein Za in the general formula (I) represents a group selected from the group consisting of C1-12 alkyl or alkoxylgroup which may be substituted by from 1 to 7 fluorine atoms.
    [13] The compound according to Claim 12, wherein Za inthe general formula (I) represents a trifluoromethoxy group.
    [14] The compound according to any one of Claims 1 to 13,wherein X1 in the general formula (I) represents a fluorine atom.
    [15] The compound according to Claim 14, wherein X2 inthe general formula (I) represents a fluorine atom.
    [16] The compound according to Claim 2 or 3, wherein X1and X2 in the general formula (I) each represent a fluorine atom.
    [17] A liquid crystal composition comprising a compoundrepresented by the general formula (I) described in Claim 1.
    [18] The liquid crystal composition according to Claim17 for use in active matrix driving.
    [19] A liquid crystal device comprising as a constituentelement a liquid crystal composition described in Claim 17.
    [20] An active matrix driving liquid crystal displaydevice comprising a liquid crystal composition described in Claim18.
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    同族专利:
    公开号 | 公开日
    CA2269561A1|1999-10-22|
    EP1452514A1|2004-09-01|
    HK1068328A1|2005-04-29|
    DE69941162D1|2009-09-03|
    US6468607B1|2002-10-22|
    HK1030595A1|2001-05-11|
    SG85639A1|2002-01-15|
    EP1452514B1|2010-03-31|
    DE69942212D1|2010-05-12|
    KR19990087956A|1999-12-27|
    DE69923024D1|2005-02-10|
    HK1050674A1|2003-07-04|
    US7145047B2|2006-12-05|
    CN1246469A|2000-03-08|
    EP1273562B1|2009-07-22|
    KR100611518B1|2006-08-11|
    US20030136944A1|2003-07-24|
    CN1291958C|2006-12-27|
    CA2269561C|2007-06-05|
    EP0952135A1|1999-10-27|
    DE69923024T2|2005-12-01|
    EP0952135B1|2005-01-05|
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    优先权:
    申请号 | 申请日 | 专利标题
    JP11214798A|JP4258033B2|1998-04-22|1998-04-22|Novel liquid crystalline compound which is 6-fluoronaphthalene derivative and liquid crystal composition containing the same|
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    JP10200352A|JP2000034240A|1998-07-15|1998-07-15|Ethynylnaphthalene derivative|
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    JP34842898A|JP4487327B2|1998-12-08|1998-12-08|NOVEL LIQUID CRYSTALLINE COMPOUND, LIQUID CRYSTALLINE COMPOSITION COMPRISING SAME, AND PROCESS FOR PRODUCING THE SAME|
    JP34842898||1998-12-08||
    EP99107369A|EP0952135B1|1998-04-22|1999-04-22|Naphthalene derivative and liquid crystal composition comprising the same|
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